# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2d_monoclin
_database_code_depnum_ccdc_archive 'CCDC 1558049'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 O4 P2 S4'
_chemical_formula_sum            'C20 H26 O4 P2 S4'
_chemical_formula_weight         520.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6554(19)
_cell_length_b                   8.5028(9)
_cell_length_c                   23.058(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.230(12)
_cell_angle_gamma                90
_cell_volume                     2433.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4847
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8581
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.183
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2762
_reflns_number_total             3264
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.6996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   fmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.43332(2) 0.24489(4) 0.34109(2) 0.01747(8) Uani 1 1 d . . . . .
S1 S 0.42224(2) 0.13443(4) 0.25824(2) 0.01997(8) Uani 1 1 d . . . . .
S2 S 0.30310(3) 0.17861(5) 0.36582(2) 0.02723(9) Uani 1 1 d . . . . .
O1 O 0.45090(7) 0.42724(11) 0.33386(4) 0.02228(19) Uani 1 1 d . . . . .
O2 O 0.85937(7) 0.06625(13) 0.48104(4) 0.0270(2) Uani 1 1 d . . . . .
C1 C 0.36609(10) 0.53047(17) 0.30286(6) 0.0251(3) Uani 1 1 d . . . . .
H1A H 0.300745 0.521791 0.320281 0.030 Uiso 1 1 calc R . . . .
H1B H 0.347019 0.501689 0.260506 0.030 Uiso 1 1 calc R . . . .
C2 C 0.41050(11) 0.69589(17) 0.30982(6) 0.0270(3) Uani 1 1 d . . . . .
H2A H 0.427647 0.722489 0.352421 0.032 Uiso 1 1 calc R . . . .
H2B H 0.354182 0.769849 0.290360 0.032 Uiso 1 1 calc R . . . .
C3 C 0.51115(10) 0.71898(16) 0.28379(6) 0.0242(3) Uani 1 1 d . . . . .
H3A H 0.563036 0.633973 0.298306 0.029 Uiso 1 1 calc R . . . .
H3B H 0.545225 0.820147 0.298167 0.029 Uiso 1 1 calc R . . . .
C10 C 0.55982(10) 0.19240(15) 0.38530(5) 0.0192(2) Uani 1 1 d . . . . .
C11 C 0.56917(11) 0.05567(17) 0.41898(6) 0.0269(3) Uani 1 1 d . . . . .
H11 H 0.506989 -0.006402 0.419608 0.032 Uiso 1 1 calc R . . . .
C12 C 0.66819(11) 0.00840(17) 0.45177(6) 0.0284(3) Uani 1 1 d . . . . .
H12 H 0.673877 -0.085493 0.474493 0.034 Uiso 1 1 calc R . . . .
C13 C 0.75886(10) 0.10036(16) 0.45087(5) 0.0214(2) Uani 1 1 d . . . . .
C14 C 0.74973(10) 0.23904(16) 0.41796(5) 0.0214(2) Uani 1 1 d . . . . .
H14 H 0.811513 0.302760 0.418315 0.026 Uiso 1 1 calc R . . . .
C15 C 0.65156(10) 0.28430(16) 0.38488(5) 0.0202(2) Uani 1 1 d . . . . .
H15 H 0.646192 0.377661 0.361860 0.024 Uiso 1 1 calc R . . . .
C16 C 0.87343(12) -0.07752(19) 0.51404(7) 0.0317(3) Uani 1 1 d . . . . .
H16A H 0.854188 -0.166638 0.487102 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.826909 -0.076914 0.543403 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.948820 -0.087347 0.534186 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.1087(5) . ?
P1 S2 1.9300(5) . ?
P1 O1 1.5798(10) . ?
P1 C10 1.7792(13) . ?
S1 S1 2.0758(6) 2_655 ?
O1 C1 1.4610(15) . ?
O2 C13 1.3570(15) . ?
O2 C16 1.4325(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.512(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5229(17) . ?
C3 C3 1.529(3) 2_655 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C10 C11 1.3902(18) . ?
C10 C15 1.4011(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3909(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3920(19) . ?
C13 C14 1.3948(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3799(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 P1 S1 103.16(2) . . ?
O1 P1 S1 109.11(4) . . ?
O1 P1 S2 117.63(4) . . ?
O1 P1 C10 100.20(5) . . ?
C10 P1 S1 107.52(4) . . ?
C10 P1 S2 118.83(4) . . ?
S1 S1 P1 105.53(2) 2_655 . ?
C1 O1 P1 122.42(8) . . ?
C13 O2 C16 117.50(11) . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
O1 C1 C2 106.53(11) . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.60(11) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 C3 113.53(14) . 2_655 ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C3 C3 H3A 108.9 2_655 . ?
C3 C3 H3B 108.9 2_655 . ?
H3A C3 H3B 107.7 . . ?
C11 C10 P1 119.94(10) . . ?
C11 C10 C15 119.32(12) . . ?
C15 C10 P1 120.70(10) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.99(12) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.19(13) . . ?
C13 C12 H12 120.4 . . ?
O2 C13 C12 124.43(12) . . ?
O2 C13 C14 115.45(11) . . ?
C12 C13 C14 120.12(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.45(12) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.91(12) . . ?
C14 C15 H15 120.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 175.35(8) . . . . ?
P1 C10 C11 C12 177.03(11) . . . . ?
P1 C10 C15 C14 -177.88(9) . . . . ?
S1 P1 O1 C1 70.67(9) . . . . ?
S1 P1 C10 C11 -87.70(11) . . . . ?
S1 P1 C10 C15 89.83(10) . . . . ?
S2 P1 O1 C1 -46.29(10) . . . . ?
S2 P1 C10 C11 28.81(12) . . . . ?
S2 P1 C10 C15 -153.67(9) . . . . ?
O1 P1 C10 C11 158.37(10) . . . . ?
O1 P1 C10 C15 -24.11(11) . . . . ?
O1 C1 C2 C3 60.33(14) . . . . ?
O2 C13 C14 C15 179.11(11) . . . . ?
C1 C2 C3 C3 72.04(12) . . . 2_655 ?
C10 P1 O1 C1 -176.62(9) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C10 C15 C14 -0.34(18) . . . . ?
C11 C12 C13 O2 179.94(13) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 -1.63(19) . . . . ?
C13 C14 C15 C10 1.42(18) . . . . ?
C15 C10 C11 C12 -0.5(2) . . . . ?
C16 O2 C13 C12 2.65(19) . . . . ?
C16 O2 C13 C14 -178.12(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2d_triclinic
_database_code_depnum_ccdc_archive 'CCDC 1558050'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 O4 P2 S4'
_chemical_formula_sum            'C20 H26 O4 P2 S4'
_chemical_formula_weight         520.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4186(13)
_cell_length_b                   10.5778(11)
_cell_length_c                   12.5703(15)
_cell_angle_alpha                71.900(9)
_cell_angle_beta                 67.807(9)
_cell_angle_gamma                82.881(9)
_cell_volume                     1219.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3058
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9505
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.360
_diffrn_reflns_theta_min         3.252
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4702
_reflns_number_total             5339
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1490P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   fmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.89494(7) -0.23440(6) 0.23767(5) 0.02072(19) Uani 1 1 d . . . . .
P2 P 0.78656(6) 0.13867(6) 0.38360(5) 0.01950(19) Uani 1 1 d . . . . .
S1 S 0.99079(6) -0.10067(6) 0.27865(6) 0.02400(19) Uani 1 1 d . . . . .
S2 S 0.84310(7) -0.06328(6) 0.43105(5) 0.02381(19) Uani 1 1 d . . . . .
S3 S 1.04887(7) -0.30558(6) 0.12753(6) 0.0280(2) Uani 1 1 d . . . . .
S4 S 0.68802(7) 0.16597(6) 0.53935(5) 0.0265(2) Uani 1 1 d . . . . .
O1 O 0.7776(2) -0.15686(19) 0.19044(16) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.70352(19) 0.16294(17) 0.29568(15) 0.0231(4) Uani 1 1 d . . . . .
O3 O 0.5703(2) -0.5913(2) 0.71203(17) 0.0313(4) Uani 1 1 d . . . . .
O4 O 1.3080(2) 0.4351(2) 0.07933(19) 0.0321(4) Uani 1 1 d . . . . .
C1 C 0.8142(3) -0.0547(3) 0.0740(2) 0.0275(5) Uani 1 1 d . . . . .
H1A H 0.894313 -0.084879 0.013593 0.033 Uiso 1 1 calc R . . . .
H1B H 0.839534 0.028848 0.080724 0.033 Uiso 1 1 calc R . . . .
C2 C 0.6889(3) -0.0320(3) 0.0367(2) 0.0282(5) Uani 1 1 d . . . . .
H2A H 0.667480 -0.115743 0.027476 0.034 Uiso 1 1 calc R . . . .
H2B H 0.711802 0.035864 -0.042331 0.034 Uiso 1 1 calc R . . . .
C3 C 0.5603(3) 0.0138(3) 0.1266(2) 0.0260(5) Uani 1 1 d . . . . .
H3A H 0.545468 -0.047408 0.207856 0.031 Uiso 1 1 calc R . . . .
H3B H 0.478490 0.007780 0.106587 0.031 Uiso 1 1 calc R . . . .
C4 C 0.5708(3) 0.1568(3) 0.1286(2) 0.0266(5) Uani 1 1 d . . . . .
H4A H 0.669811 0.179128 0.101289 0.032 Uiso 1 1 calc R . . . .
H4B H 0.531583 0.218774 0.071153 0.032 Uiso 1 1 calc R . . . .
C5 C 0.4957(3) 0.1776(3) 0.2516(2) 0.0253(5) Uani 1 1 d . . . . .
H5A H 0.490938 0.274125 0.243269 0.030 Uiso 1 1 calc R . . . .
H5B H 0.399468 0.145208 0.283053 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5640(3) 0.1075(3) 0.3414(2) 0.0238(5) Uani 1 1 d . . . . .
H6A H 0.509255 0.121856 0.420478 0.029 Uiso 1 1 calc R . . . .
H6B H 0.569977 0.010659 0.351050 0.029 Uiso 1 1 calc R . . . .
C10 C 0.7945(3) -0.3455(2) 0.3764(2) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.8624(3) -0.4510(2) 0.4348(2) 0.0249(5) Uani 1 1 d . . . . .
H11 H 0.958649 -0.465418 0.396617 0.030 Uiso 1 1 calc R . . . .
C12 C 0.7913(3) -0.5347(2) 0.5474(2) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.838460 -0.605216 0.586455 0.031 Uiso 1 1 calc R . . . .
C13 C 0.6503(3) -0.5138(2) 0.6023(2) 0.0240(5) Uani 1 1 d . . . . .
C14 C 0.5806(3) -0.4102(3) 0.5450(2) 0.0270(5) Uani 1 1 d . . . . .
H14 H 0.483936 -0.397299 0.582495 0.032 Uiso 1 1 calc R . . . .
C15 C 0.6529(3) -0.3266(2) 0.4335(2) 0.0243(5) Uani 1 1 d . . . . .
H15 H 0.605675 -0.255366 0.395370 0.029 Uiso 1 1 calc R . . . .
C16 C 0.6393(4) -0.6886(3) 0.7803(2) 0.0343(6) Uani 1 1 d . . . . .
H16A H 0.689128 -0.751741 0.735387 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.570857 -0.736461 0.856946 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.705333 -0.644391 0.795333 0.051 Uiso 1 1 calc GR . . . .
C20 C 0.9393(3) 0.2324(2) 0.2878(2) 0.0216(5) Uani 1 1 d . . . . .
C21 C 1.0261(3) 0.2606(2) 0.3391(2) 0.0240(5) Uani 1 1 d . . . . .
H21 H 1.001005 0.233150 0.423775 0.029 Uiso 1 1 calc R . . . .
C22 C 1.1485(3) 0.3283(3) 0.2670(2) 0.0265(5) Uani 1 1 d . . . . .
H22 H 1.207453 0.347174 0.302101 0.032 Uiso 1 1 calc R . . . .
C23 C 1.1855(3) 0.3688(2) 0.1426(2) 0.0236(5) Uani 1 1 d . . . . .
C24 C 1.0997(3) 0.3426(3) 0.0896(2) 0.0263(5) Uani 1 1 d . . . . .
H24 H 1.124112 0.371813 0.004996 0.032 Uiso 1 1 calc R . . . .
C25 C 0.9778(3) 0.2731(3) 0.1629(2) 0.0255(5) Uani 1 1 d . . . . .
H25 H 0.919714 0.252766 0.127678 0.031 Uiso 1 1 calc R . . . .
C26 C 1.3468(3) 0.4830(3) -0.0478(3) 0.0387(7) Uani 1 1 d . . . . .
H26A H 1.439852 0.521156 -0.083219 0.058 Uiso 1 1 calc GR . . . .
H26B H 1.280543 0.551532 -0.068028 0.058 Uiso 1 1 calc GR . . . .
H26C H 1.346624 0.409299 -0.079460 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.1108(8) . ?
P1 S3 1.9305(9) . ?
P1 O1 1.5869(19) . ?
P1 C10 1.780(3) . ?
P2 S2 2.1043(9) . ?
P2 S4 1.9313(9) . ?
P2 O2 1.5896(17) . ?
P2 C20 1.780(2) . ?
S1 S2 2.0705(9) . ?
O1 C1 1.467(3) . ?
O2 C6 1.469(3) . ?
O3 C13 1.366(3) . ?
O3 C16 1.431(3) . ?
O4 C23 1.364(3) . ?
O4 C26 1.426(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.515(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.530(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.512(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C10 C11 1.405(3) . ?
C10 C15 1.396(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(4) . ?
C13 C14 1.398(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.396(3) . ?
C20 C25 1.400(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.394(4) . ?
C23 C24 1.395(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(4) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S3 P1 S1 103.16(4) . . ?
O1 P1 S1 108.66(8) . . ?
O1 P1 S3 117.48(8) . . ?
O1 P1 C10 101.38(11) . . ?
C10 P1 S1 107.10(8) . . ?
C10 P1 S3 118.54(9) . . ?
S4 P2 S2 101.39(4) . . ?
O2 P2 S2 109.73(7) . . ?
O2 P2 S4 117.54(8) . . ?
O2 P2 C20 101.32(10) . . ?
C20 P2 S2 108.26(9) . . ?
C20 P2 S4 118.40(8) . . ?
S2 S1 P1 104.81(4) . . ?
S1 S2 P2 107.23(4) . . ?
C1 O1 P1 120.49(17) . . ?
C6 O2 P2 119.62(15) . . ?
C13 O3 C16 117.6(2) . . ?
C23 O4 C26 117.3(2) . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
O1 C1 C2 107.6(2) . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 C3 113.1(2) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.5(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.4(2) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.6(2) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
O2 C6 C5 107.60(19) . . ?
O2 C6 H6A 110.2 . . ?
O2 C6 H6B 110.2 . . ?
C5 C6 H6A 110.2 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C11 C10 P1 118.6(2) . . ?
C15 C10 P1 122.66(19) . . ?
C15 C10 C11 118.6(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
O3 C13 C12 123.9(2) . . ?
O3 C13 C14 115.6(2) . . ?
C12 C13 C14 120.5(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 118.69(19) . . ?
C21 C20 C25 119.3(2) . . ?
C25 C20 P2 121.95(18) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
O4 C23 C22 115.6(2) . . ?
O4 C23 C24 123.7(2) . . ?
C22 C23 C24 120.7(2) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.7(2) . . ?
C25 C24 H24 120.6 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 162.12(18) . . . . ?
P1 C10 C11 C12 175.04(18) . . . . ?
P1 C10 C15 C14 -175.68(19) . . . . ?
P2 O2 C6 C5 163.87(17) . . . . ?
P2 C20 C21 C22 177.3(2) . . . . ?
P2 C20 C25 C24 -178.0(2) . . . . ?
S1 P1 O1 C1 68.91(19) . . . . ?
S1 P1 C10 C11 -79.16(19) . . . . ?
S1 P1 C10 C15 96.2(2) . . . . ?
S2 P2 O2 C6 68.96(18) . . . . ?
S2 P2 C20 C21 -78.7(2) . . . . ?
S2 P2 C20 C25 98.3(2) . . . . ?
S3 P1 O1 C1 -47.6(2) . . . . ?
S3 P1 C10 C11 36.8(2) . . . . ?
S3 P1 C10 C15 -147.81(17) . . . . ?
S4 P2 O2 C6 -46.1(2) . . . . ?
S4 P2 C20 C21 35.8(2) . . . . ?
S4 P2 C20 C25 -147.18(19) . . . . ?
O1 P1 C10 C11 167.05(18) . . . . ?
O1 P1 C10 C15 -17.6(2) . . . . ?
O1 C1 C2 C3 59.4(3) . . . . ?
O2 P2 C20 C21 165.91(19) . . . . ?
O2 P2 C20 C25 -17.1(2) . . . . ?
O3 C13 C14 C15 -179.9(2) . . . . ?
O4 C23 C24 C25 179.4(2) . . . . ?
C1 C2 C3 C4 70.8(3) . . . . ?
C2 C3 C4 C5 -147.2(2) . . . . ?
C3 C4 C5 C6 69.5(3) . . . . ?
C4 C5 C6 O2 61.7(3) . . . . ?
C10 P1 O1 C1 -178.47(18) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C11 C12 C13 O3 179.0(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C10 1.0(4) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C16 O3 C13 C12 8.2(3) . . . . ?
C16 O3 C13 C14 -172.9(2) . . . . ?
C20 P2 O2 C6 -176.75(18) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C20 C25 C24 -1.0(4) . . . . ?
C21 C22 C23 O4 179.9(2) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C22 C23 C24 C25 -1.3(4) . . . . ?
C23 C24 C25 C20 1.5(4) . . . . ?
C25 C20 C21 C22 0.2(4) . . . . ?
C26 O4 C23 C22 -177.5(2) . . . . ?
C26 O4 C23 C24 1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_znowy
_database_code_depnum_ccdc_archive 'CCDC 1948450'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 O3 P S'
_chemical_formula_sum            'C9 H11 O3 P S'
_chemical_formula_weight         230.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6103(15)
_cell_length_b                   7.7451(11)
_cell_length_c                   20.145(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.289(17)
_cell_angle_gamma                90
_cell_volume                     1028.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1422
_cell_measurement_temperature    120
_cell_measurement_theta_max      22.46
_cell_measurement_theta_min      2.05
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6754
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.095
_diffrn_reflns_theta_max         25.095
_diffrn_reflns_theta_min         2.819
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1479
_reflns_number_total             1822
_reflns_special_details          'Friedel pairs have been merged'
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.242
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0848
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1883P)²+0.4498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2239
_refine_ls_wR_factor_ref         0.2384
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23830(15) 0.80070(15) 0.09807(6) 0.0273(5) Uani 1 1 d . . . . .
P1 P 0.52630(15) 0.76536(14) 0.10246(5) 0.0204(4) Uani 1 1 d . . . . .
O1 O 0.9343(5) 0.8092(4) 0.37389(15) 0.0273(8) Uani 1 1 d . . . . .
O2 O 0.5981(4) 0.5882(4) 0.06974(14) 0.0245(8) Uani 1 1 d . . . . .
O3 O 0.6515(4) 0.8942(4) 0.05858(15) 0.0256(8) Uani 1 1 d . . . . .
C3 C 0.9335(6) 0.6992(6) 0.2609(2) 0.0272(11) Uani 1 1 d . . . . .
H3 H 1.059836 0.641959 0.269536 0.033 Uiso 1 1 calc R . . . .
C4 C 0.8477(6) 0.7893(5) 0.3112(2) 0.0221(10) Uani 1 1 d . . . . .
C1 C 0.6451(6) 0.7732(5) 0.1848(2) 0.0212(9) Uani 1 1 d . . . . .
C9 C 0.7483(6) 0.6190(6) 0.0218(2) 0.0240(10) Uani 1 1 d . . . . .
H9A H 0.728044 0.539253 -0.016508 0.029 Uiso 1 1 calc R . . . .
H9B H 0.887429 0.603604 0.042742 0.029 Uiso 1 1 calc R . . . .
C2 C 0.8347(6) 0.6930(5) 0.1981(2) 0.0237(10) Uani 1 1 d . . . . .
H2 H 0.895648 0.633802 0.163437 0.028 Uiso 1 1 calc R . . . .
C7 C 1.1212(6) 0.7175(6) 0.3905(2) 0.0290(11) Uani 1 1 d . . . . .
H7A H 1.223376 0.753902 0.360565 0.044 Uiso 1 1 calc GR . . . .
H7B H 1.097508 0.593069 0.385599 0.044 Uiso 1 1 calc GR . . . .
H7C H 1.169621 0.743162 0.436603 0.044 Uiso 1 1 calc GR . . . .
C8 C 0.7128(7) 0.8056(6) -0.0002(2) 0.0286(10) Uani 1 1 d . . . . .
H8A H 0.838637 0.856760 -0.015352 0.034 Uiso 1 1 calc R . . . .
H8B H 0.604904 0.812446 -0.036920 0.034 Uiso 1 1 calc R . . . .
C6 C 0.5607(6) 0.8603(6) 0.2360(2) 0.0254(10) Uani 1 1 d . . . . .
H6 H 0.432925 0.915568 0.227808 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6584(6) 0.8683(6) 0.2985(2) 0.0276(10) Uani 1 1 d . . . . .
H5 H 0.597416 0.927532 0.333180 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 1.9189(14) . ?
P1 O2 1.609(3) . ?
P1 O3 1.604(3) . ?
P1 C1 1.782(4) . ?
O1 C4 1.355(5) . ?
O1 C7 1.442(5) . ?
O2 C9 1.455(4) . ?
O3 C8 1.452(5) . ?
C3 C4 1.387(6) . ?
C3 C2 1.379(6) . ?
C4 C5 1.400(6) . ?
C1 C2 1.407(6) . ?
C1 C6 1.386(6) . ?
C9 C8 1.525(7) . ?
C6 C5 1.372(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 S1 115.14(12) . . ?
O2 P1 C1 106.69(18) . . ?
O3 P1 S1 115.90(13) . . ?
O3 P1 O2 97.17(15) . . ?
O3 P1 C1 106.40(17) . . ?
C1 P1 S1 113.86(14) . . ?
C4 O1 C7 117.0(3) . . ?
C9 O2 P1 111.6(3) . . ?
C8 O3 P1 110.0(3) . . ?
C2 C3 C4 119.8(4) . . ?
O1 C4 C3 124.9(4) . . ?
O1 C4 C5 115.5(4) . . ?
C3 C4 C5 119.7(4) . . ?
C2 C1 P1 119.2(3) . . ?
C6 C1 P1 122.4(3) . . ?
C6 C1 C2 118.4(4) . . ?
O2 C9 C8 104.5(3) . . ?
C3 C2 C1 120.9(4) . . ?
O3 C8 C9 104.9(3) . . ?
C5 C6 C1 121.1(4) . . ?
C6 C5 C4 120.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 P1 O2 C9 127.6(2) . . . . ?
S1 P1 O3 C8 -104.9(3) . . . . ?
S1 P1 C1 C2 158.2(3) . . . . ?
S1 P1 C1 C6 -23.9(4) . . . . ?
P1 O2 C9 C8 -23.5(4) . . . . ?
P1 O3 C8 C9 -32.7(4) . . . . ?
P1 C1 C2 C3 178.7(3) . . . . ?
P1 C1 C6 C5 -178.1(3) . . . . ?
O1 C4 C5 C6 178.0(4) . . . . ?
O2 P1 O3 C8 17.6(3) . . . . ?
O2 P1 C1 C2 30.1(4) . . . . ?
O2 P1 C1 C6 -152.1(3) . . . . ?
O2 C9 C8 O3 34.2(4) . . . . ?
O3 P1 O2 C9 4.5(3) . . . . ?
O3 P1 C1 C2 -72.9(4) . . . . ?
O3 P1 C1 C6 105.0(4) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
C4 C3 C2 C1 -1.7(6) . . . . ?
C1 P1 O2 C9 -105.0(3) . . . . ?
C1 P1 O3 C8 127.4(3) . . . . ?
C1 C6 C5 C4 0.7(7) . . . . ?
C2 C3 C4 O1 -177.5(4) . . . . ?
C2 C3 C4 C5 2.1(6) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
C7 O1 C4 C3 -5.5(6) . . . . ?
C7 O1 C4 C5 174.9(4) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3c_trans
_database_code_depnum_ccdc_archive 'CCDC 1558052'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 O4 P2 S3'
_chemical_formula_sum            'C18 H22 O4 P2 S3'
_chemical_formula_weight         460.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5551(6)
_cell_length_b                   10.9717(8)
_cell_length_c                   13.0957(10)
_cell_angle_alpha                113.352(7)
_cell_angle_beta                 104.434(7)
_cell_angle_gamma                93.127(6)
_cell_volume                     1076.52(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1794
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6586
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.496
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'KM4CCD, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             3990
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+1.1001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.96538(15) 0.48899(15) 0.25491(12) 0.0462(4) Uani 1 1 d . . . . .
P2 P 0.60154(15) 0.32095(14) 0.20938(12) 0.0443(4) Uani 1 1 d . . . . .
S1 S 0.84253(15) 0.38769(15) 0.32778(12) 0.0503(4) Uani 1 1 d . . . . .
S2 S 1.16573(16) 0.59573(17) 0.37239(14) 0.0648(5) Uani 1 1 d . . . . .
S3 S 0.58149(17) 0.20629(16) 0.05013(13) 0.0602(5) Uani 1 1 d . . . . .
O1 O 0.8364(4) 0.5672(3) 0.2079(3) 0.0447(9) Uani 1 1 d . . . . .
O2 O 0.5373(4) 0.4601(3) 0.2358(3) 0.0490(9) Uani 1 1 d . . . . .
O3 O 1.0465(4) 0.0920(4) -0.1862(3) 0.0636(11) Uani 1 1 d . . . . .
O4 O 0.2931(6) 0.0974(4) 0.4712(4) 0.0802(14) Uani 1 1 d . . . . .
C1 C 0.8012(6) 0.6918(5) 0.2870(5) 0.0534(15) Uani 1 1 d . . . . .
H1A H 0.895302 0.763100 0.318051 0.064 Uiso 1 1 calc R . . . .
H1B H 0.777742 0.679974 0.351603 0.064 Uiso 1 1 calc R . . . .
C2 C 0.6561(6) 0.7289(6) 0.2214(5) 0.0521(14) Uani 1 1 d . . . . .
H2A H 0.667154 0.710714 0.145029 0.062 Uiso 1 1 calc R . . . .
H2B H 0.660466 0.825267 0.261463 0.062 Uiso 1 1 calc R . . . .
C3 C 0.4863(6) 0.6581(6) 0.2048(5) 0.0591(16) Uani 1 1 d . . . . .
H3A H 0.467348 0.688215 0.280407 0.071 Uiso 1 1 calc R . . . .
H3B H 0.404962 0.687256 0.157222 0.071 Uiso 1 1 calc R . . . .
C4 C 0.4582(6) 0.5057(6) 0.1495(5) 0.0643(17) Uani 1 1 d . . . . .
H4A H 0.341691 0.470439 0.120721 0.077 Uiso 1 1 calc R . . . .
H4B H 0.503264 0.473432 0.084400 0.077 Uiso 1 1 calc R . . . .
C10 C 0.9887(5) 0.3687(5) 0.1222(4) 0.0423(12) Uani 1 1 d . . . . .
C11 C 0.9177(6) 0.3704(5) 0.0165(5) 0.0484(13) Uani 1 1 d . . . . .
H11 H 0.853418 0.435194 0.013088 0.058 Uiso 1 1 calc R . . . .
C12 C 0.9402(6) 0.2776(6) -0.0849(5) 0.0543(14) Uani 1 1 d . . . . .
H12 H 0.892454 0.281205 -0.155439 0.065 Uiso 1 1 calc R . . . .
C13 C 1.0339(6) 0.1790(6) -0.0814(5) 0.0492(14) Uani 1 1 d . . . . .
C14 C 1.1064(6) 0.1758(6) 0.0235(5) 0.0569(15) Uani 1 1 d . . . . .
H14 H 1.169679 0.110244 0.026297 0.068 Uiso 1 1 calc R . . . .
C15 C 1.0852(6) 0.2703(6) 0.1256(5) 0.0521(14) Uani 1 1 d . . . . .
H15 H 1.135336 0.268212 0.196476 0.063 Uiso 1 1 calc R . . . .
C16 C 1.1345(8) -0.0167(6) -0.1904(6) 0.084(2) Uani 1 1 d . . . . .
H16A H 1.133554 -0.069622 -0.269187 0.126 Uiso 1 1 calc R . . . .
H16B H 1.245625 0.019134 -0.142013 0.126 Uiso 1 1 calc R . . . .
H16C H 1.083160 -0.072492 -0.162877 0.126 Uiso 1 1 calc R . . . .
C20 C 0.5045(5) 0.2473(5) 0.2838(4) 0.0414(12) Uani 1 1 d . . . . .
C21 C 0.4601(7) 0.1111(6) 0.2437(5) 0.0583(16) Uani 1 1 d . . . . .
H21 H 0.479218 0.054141 0.175020 0.070 Uiso 1 1 calc R . . . .
C22 C 0.3876(6) 0.0557(6) 0.3021(5) 0.0589(16) Uani 1 1 d . . . . .
H22 H 0.358643 -0.037298 0.273295 0.071 Uiso 1 1 calc R . . . .
C23 C 0.3588(6) 0.1397(6) 0.4036(5) 0.0514(14) Uani 1 1 d . . . . .
C24 C 0.3970(8) 0.2762(6) 0.4420(6) 0.079(2) Uani 1 1 d . . . . .
H24 H 0.373755 0.333357 0.508923 0.094 Uiso 1 1 calc R . . . .
C25 C 0.4696(7) 0.3303(6) 0.3827(5) 0.0653(17) Uani 1 1 d . . . . .
H25 H 0.494959 0.423372 0.409851 0.078 Uiso 1 1 calc R . . . .
C26 C 0.2530(8) -0.0418(7) 0.4388(6) 0.083(2) Uani 1 1 d . . . . .
H26A H 0.208357 -0.055245 0.494653 0.124 Uiso 1 1 calc R . . . .
H26B H 0.173512 -0.083278 0.363294 0.124 Uiso 1 1 calc R . . . .
H26C H 0.349922 -0.081709 0.436351 0.124 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.113(2) . ?
P1 S2 1.9273(19) . ?
P1 O1 1.586(4) . ?
P1 C10 1.784(5) . ?
P2 S1 2.1290(18) . ?
P2 S3 1.918(2) . ?
P2 O2 1.588(4) . ?
P2 C20 1.802(5) . ?
O1 C1 1.453(6) . ?
O2 C4 1.445(6) . ?
O3 C13 1.361(6) . ?
O3 C16 1.435(7) . ?
O4 C23 1.364(6) . ?
O4 C26 1.410(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.498(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.532(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.513(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 C11 1.375(7) . ?
C10 C15 1.402(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(7) . ?
C13 C14 1.376(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(7) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 C21 1.367(7) . ?
C20 C25 1.373(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(7) . ?
C23 C24 1.368(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(8) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 P1 S1 107.63(9) . . ?
O1 P1 S1 105.46(13) . . ?
O1 P1 S2 117.14(15) . . ?
O1 P1 C10 101.2(2) . . ?
C10 P1 S1 109.08(18) . . ?
C10 P1 S2 115.66(16) . . ?
S3 P2 S1 116.83(8) . . ?
O2 P2 S1 100.78(15) . . ?
O2 P2 S3 117.54(16) . . ?
O2 P2 C20 103.6(2) . . ?
C20 P2 S1 99.51(16) . . ?
C20 P2 S3 115.90(18) . . ?
P1 S1 P2 103.01(8) . . ?
C1 O1 P1 120.9(3) . . ?
C4 O2 P2 125.6(4) . . ?
C13 O3 C16 118.5(5) . . ?
C23 O4 C26 119.4(5) . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O1 C1 C2 108.6(4) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
C1 C2 H2A 108.0 . . ?
C1 C2 H2B 108.0 . . ?
C1 C2 C3 117.1(5) . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 H2A 108.0 . . ?
C3 C2 H2B 108.0 . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 116.1(5) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
O2 C4 C3 108.9(5) . . ?
O2 C4 H4A 109.9 . . ?
O2 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C11 C10 P1 122.3(4) . . ?
C11 C10 C15 118.6(5) . . ?
C15 C10 P1 119.2(4) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(5) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C13 C12 H12 119.9 . . ?
O3 C13 C12 115.3(5) . . ?
O3 C13 C14 125.1(5) . . ?
C14 C13 C12 119.6(5) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 122.4(4) . . ?
C21 C20 C25 118.4(5) . . ?
C25 C20 P2 119.2(4) . . ?
C20 C21 H21 119.0 . . ?
C20 C21 C22 121.9(5) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.2(5) . . ?
C23 C22 H22 120.4 . . ?
O4 C23 C22 124.8(5) . . ?
O4 C23 C24 115.8(5) . . ?
C24 C23 C22 119.4(5) . . ?
C23 C24 H24 119.6 . . ?
C23 C24 C25 120.8(6) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 120.2(5) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 -170.4(3) . . . . ?
P1 C10 C11 C12 178.8(4) . . . . ?
P1 C10 C15 C14 -179.6(4) . . . . ?
P2 O2 C4 C3 -154.0(4) . . . . ?
P2 C20 C21 C22 179.2(4) . . . . ?
P2 C20 C25 C24 -179.3(5) . . . . ?
S1 P1 O1 C1 77.5(3) . . . . ?
S1 P1 C10 C11 117.4(4) . . . . ?
S1 P1 C10 C15 -63.8(4) . . . . ?
S1 P2 O2 C4 131.0(4) . . . . ?
S1 P2 C20 C21 -108.4(4) . . . . ?
S1 P2 C20 C25 73.4(4) . . . . ?
S2 P1 O1 C1 -42.1(4) . . . . ?
S2 P1 C10 C11 -121.1(4) . . . . ?
S2 P1 C10 C15 57.6(4) . . . . ?
S3 P2 O2 C4 2.9(4) . . . . ?
S3 P2 C20 C21 17.8(5) . . . . ?
S3 P2 C20 C25 -160.4(4) . . . . ?
O1 P1 C10 C11 6.6(5) . . . . ?
O1 P1 C10 C15 -174.7(4) . . . . ?
O1 C1 C2 C3 81.4(6) . . . . ?
O2 P2 C20 C21 148.0(4) . . . . ?
O2 P2 C20 C25 -30.2(5) . . . . ?
O3 C13 C14 C15 179.9(5) . . . . ?
O4 C23 C24 C25 177.7(6) . . . . ?
C1 C2 C3 C4 -54.6(7) . . . . ?
C2 C3 C4 O2 77.3(6) . . . . ?
C10 P1 O1 C1 -168.8(3) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C11 C10 C15 C14 -0.8(7) . . . . ?
C11 C12 C13 O3 179.3(5) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C13 C14 C15 C10 0.6(8) . . . . ?
C15 C10 C11 C12 0.0(8) . . . . ?
C16 O3 C13 C12 -176.9(5) . . . . ?
C16 O3 C13 C14 3.5(8) . . . . ?
C20 P2 O2 C4 -126.4(4) . . . . ?
C20 C21 C22 C23 0.2(9) . . . . ?
C21 C20 C25 C24 2.5(9) . . . . ?
C21 C22 C23 O4 -177.8(5) . . . . ?
C21 C22 C23 C24 2.4(9) . . . . ?
C22 C23 C24 C25 -2.5(10) . . . . ?
C23 C24 C25 C20 0.0(10) . . . . ?
C25 C20 C21 C22 -2.6(9) . . . . ?
C26 O4 C23 C22 1.3(9) . . . . ?
C26 O4 C23 C24 -178.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a_trans
_database_code_depnum_ccdc_archive 'CCDC 1558051'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O4 P2 S3'
_chemical_formula_sum            'C16 H18 O4 P2 S3'
_chemical_formula_weight         432.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2217(5)
_cell_length_b                   15.7169(6)
_cell_length_c                   33.5977(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.598(5)
_cell_angle_gamma                90
_cell_volume                     3809.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15703
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.61
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.851
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15794
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.234
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         .
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5071
_reflns_number_total             7366
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+3.0897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C50(H50A,H50B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24),
 C25(H25), C31(H31), C32(H32), C34(H34), C35(H35), C41(H41), C42(H42), C45(H45),
  C46(H46)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C36(H36A,H36B,H36C), C47(H47A,H47B,
 H47C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.16784(13) 0.82123(6) 0.16140(2) 0.0162(2) Uani 1 1 d . . . . .
P2 P 0.34037(13) 0.74597(6) 0.07667(2) 0.0163(2) Uani 1 1 d . . . . .
S1 S 0.42003(12) 0.79750(6) 0.13319(2) 0.0178(2) Uani 1 1 d . . . . .
S2 S 0.02084(13) 0.72365(7) 0.17393(3) 0.0235(2) Uani 1 1 d . . . . .
S3 S 0.49106(14) 0.79748(7) 0.03722(3) 0.0257(2) Uani 1 1 d . . . . .
O1 O 0.0693(3) 0.89125(17) 0.13374(7) 0.0208(6) Uani 1 1 d . . . . .
O2 O 0.1230(3) 0.76093(17) 0.07167(7) 0.0185(6) Uani 1 1 d . . . . .
O3 O 0.3830(4) 1.0273(2) 0.30287(8) 0.0350(8) Uani 1 1 d . . . . .
O4 O 0.3510(4) 0.36949(18) 0.08867(8) 0.0258(6) Uani 1 1 d . . . . .
C1 C -0.0608(5) 0.8705(3) 0.10107(10) 0.0239(9) Uani 1 1 d . . . . .
H1A H -0.139696 0.920521 0.094599 0.029 Uiso 1 1 calc R . . . .
H1B H -0.142214 0.823419 0.109125 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0403(5) 0.8444(3) 0.06482(10) 0.0217(8) Uani 1 1 d . . . . .
H2A H -0.047249 0.842353 0.041289 0.026 Uiso 1 1 calc R . . . .
H2B H 0.138138 0.886500 0.059530 0.026 Uiso 1 1 calc R . . . .
C10 C 0.2484(5) 0.8846(2) 0.20267(9) 0.0178(8) Uani 1 1 d . . . . .
C11 C 0.2871(5) 0.8462(3) 0.23975(10) 0.0219(8) Uani 1 1 d . . . . .
H11 H 0.280444 0.786141 0.242313 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3347(5) 0.8955(3) 0.27241(10) 0.0257(9) Uani 1 1 d . . . . .
H12 H 0.361277 0.869522 0.297557 0.031 Uiso 1 1 calc R . . . .
C13 C 0.3439(5) 0.9833(3) 0.26859(10) 0.0253(9) Uani 1 1 d . . . . .
C14 C 0.3112(5) 1.0219(3) 0.23191(10) 0.0226(8) Uani 1 1 d . . . . .
H14 H 0.321261 1.081907 0.229290 0.027 Uiso 1 1 calc R . . . .
C15 C 0.2634(5) 0.9717(3) 0.19894(10) 0.0202(8) Uani 1 1 d . . . . .
H15 H 0.240986 0.997585 0.173629 0.024 Uiso 1 1 calc R . . . .
C16 C 0.3886(7) 1.1177(3) 0.30038(13) 0.0414(12) Uani 1 1 d . . . . .
H16A H 0.276073 1.138361 0.286102 0.062 Uiso 1 1 calc GR . . . .
H16B H 0.497550 1.135162 0.286038 0.062 Uiso 1 1 calc GR . . . .
H16C H 0.396118 1.141925 0.327292 0.062 Uiso 1 1 calc GR . . . .
C20 C 0.3511(5) 0.6326(2) 0.08056(10) 0.0161(7) Uani 1 1 d . . . . .
C21 C 0.3151(5) 0.5904(3) 0.11606(10) 0.0205(8) Uani 1 1 d . . . . .
H21 H 0.289169 0.622104 0.139215 0.025 Uiso 1 1 calc R . . . .
C22 C 0.3172(5) 0.5028(3) 0.11743(10) 0.0220(8) Uani 1 1 d . . . . .
H22 H 0.293156 0.474640 0.141692 0.026 Uiso 1 1 calc R . . . .
C23 C 0.3539(5) 0.4548(2) 0.08386(11) 0.0189(8) Uani 1 1 d . . . . .
C24 C 0.3878(5) 0.4965(3) 0.04845(10) 0.0223(8) Uani 1 1 d . . . . .
H24 H 0.410918 0.464568 0.025183 0.027 Uiso 1 1 calc R . . . .
C25 C 0.3878(5) 0.5845(3) 0.04706(10) 0.0194(8) Uani 1 1 d . . . . .
H25 H 0.413362 0.612528 0.022862 0.023 Uiso 1 1 calc R . . . .
C26 C 0.4025(6) 0.3179(3) 0.05583(12) 0.0278(9) Uani 1 1 d . . . . .
H26A H 0.316828 0.328381 0.032898 0.042 Uiso 1 1 calc GR . . . .
H26B H 0.396917 0.257689 0.063335 0.042 Uiso 1 1 calc GR . . . .
H26C H 0.528952 0.332179 0.048786 0.042 Uiso 1 1 calc GR . . . .
P3 P -0.31809(13) 1.09010(6) 0.15630(3) 0.0183(2) Uani 1 1 d . . . . .
P4 P -0.12283(13) 1.15203(6) 0.07271(3) 0.0178(2) Uani 1 1 d . . . . .
S4 S -0.05683(12) 1.11353(6) 0.13205(2) 0.0192(2) Uani 1 1 d . . . . .
S5 S -0.46928(14) 1.18880(7) 0.16446(3) 0.0294(2) Uani 1 1 d . . . . .
S6 S 0.03165(15) 1.08855(7) 0.03787(3) 0.0275(2) Uani 1 1 d . . . . .
O5 O -0.4071(4) 1.01706(17) 0.12864(7) 0.0233(6) Uani 1 1 d . . . . .
O6 O -0.3404(3) 1.13818(17) 0.06614(7) 0.0211(6) Uani 1 1 d . . . . .
O7 O -0.1147(4) 0.90150(19) 0.30421(7) 0.0276(7) Uani 1 1 d . . . . .
O8 O -0.1151(4) 1.52729(18) 0.05795(8) 0.0258(6) Uani 1 1 d . . . . .
C30 C -0.2464(5) 1.0307(2) 0.19951(10) 0.0182(8) Uani 1 1 d . . . . .
C31 C -0.1918(5) 1.0733(3) 0.23462(10) 0.0233(8) Uani 1 1 d . . . . .
H31 H -0.185754 1.133725 0.234936 0.028 Uiso 1 1 calc R . . . .
C32 C -0.1470(5) 1.0280(3) 0.26865(10) 0.0243(9) Uani 1 1 d . . . . .
H32 H -0.109548 1.057361 0.292394 0.029 Uiso 1 1 calc R . . . .
C33 C -0.1559(5) 0.9398(3) 0.26867(10) 0.0218(8) Uani 1 1 d . . . . .
C34 C -0.2063(5) 0.8961(3) 0.23383(10) 0.0221(8) Uani 1 1 d . . . . .
H34 H -0.209503 0.835705 0.233557 0.027 Uiso 1 1 calc R . . . .
C35 C -0.2519(5) 0.9422(3) 0.19942(10) 0.0190(8) Uani 1 1 d . . . . .
H35 H -0.287288 0.912828 0.175546 0.023 Uiso 1 1 calc R . . . .
C36 C -0.1397(6) 0.8116(3) 0.30661(12) 0.0355(11) Uani 1 1 d . . . . .
H36A H -0.263365 0.796545 0.295591 0.053 Uiso 1 1 calc GR . . . .
H36B H -0.127439 0.793611 0.334532 0.053 Uiso 1 1 calc GR . . . .
H36C H -0.045546 0.782898 0.291347 0.053 Uiso 1 1 calc GR . . . .
C40 C -0.1087(5) 1.2650(2) 0.07070(10) 0.0170(8) Uani 1 1 d . . . . .
C41 C -0.1556(5) 1.3163(3) 0.10307(10) 0.0212(8) Uani 1 1 d . . . . .
H41 H -0.186563 1.290199 0.127384 0.025 Uiso 1 1 calc R . . . .
C42 C -0.1574(5) 1.4032(3) 0.10013(10) 0.0213(8) Uani 1 1 d . . . . .
H42 H -0.186988 1.436777 0.122483 0.026 Uiso 1 1 calc R . . . .
C44 C -0.1158(5) 1.4426(3) 0.06433(10) 0.0209(8) Uani 1 1 d . . . . .
C45 C -0.0694(5) 1.3922(3) 0.03187(10) 0.0213(8) Uani 1 1 d . . . . .
H45 H -0.039718 1.418535 0.007508 0.026 Uiso 1 1 calc R . . . .
C46 C -0.0663(5) 1.3048(3) 0.03499(10) 0.0192(8) Uani 1 1 d . . . . .
H46 H -0.035216 1.271306 0.012724 0.023 Uiso 1 1 calc R . . . .
C47 C -0.1623(6) 1.5815(3) 0.09033(12) 0.0307(10) Uani 1 1 d . . . . .
H47A H -0.159243 1.641069 0.081702 0.046 Uiso 1 1 calc GR . . . .
H47B H -0.072923 1.573157 0.112808 0.046 Uiso 1 1 calc GR . . . .
H47C H -0.287081 1.567442 0.098595 0.046 Uiso 1 1 calc GR . . . .
C50 C -0.5344(6) 1.0340(3) 0.09489(11) 0.0285(10) Uani 1 1 d . . . . .
H50A H -0.618186 1.081357 0.101481 0.034 Uiso 1 1 calc R . . . .
H50B H -0.611164 0.982981 0.089034 0.034 Uiso 1 1 calc R . . . .
C51 C -0.4293(6) 1.0571(3) 0.05897(11) 0.0267(9) Uani 1 1 d . . . . .
H51A H -0.335089 1.013027 0.054057 0.032 Uiso 1 1 calc R . . . .
H51B H -0.515084 1.060701 0.035200 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.1240(13) . ?
P1 S2 1.9227(14) . ?
P1 O1 1.588(3) . ?
P1 C10 1.783(3) . ?
P2 S1 2.1199(12) . ?
P2 S3 1.9304(13) . ?
P2 O2 1.589(2) . ?
P2 C20 1.788(4) . ?
O1 C1 1.449(4) . ?
O2 C2 1.455(4) . ?
O3 C13 1.362(4) . ?
O3 C16 1.424(6) . ?
O4 C23 1.350(5) . ?
O4 C26 1.432(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.505(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 C11 1.400(5) . ?
C10 C15 1.379(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(6) . ?
C13 C14 1.384(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.400(5) . ?
C20 C25 1.391(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(5) . ?
C23 C24 1.390(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
P3 S4 2.1210(13) . ?
P3 S5 1.9238(14) . ?
P3 O5 1.594(3) . ?
P3 C30 1.783(3) . ?
P4 S4 2.1169(12) . ?
P4 S6 1.9309(14) . ?
P4 O6 1.591(3) . ?
P4 C40 1.781(4) . ?
O5 C50 1.452(4) . ?
O6 C51 1.442(5) . ?
O7 C33 1.358(4) . ?
O7 C36 1.427(5) . ?
O8 C44 1.348(5) . ?
O8 C47 1.436(5) . ?
C30 C31 1.398(5) . ?
C30 C35 1.391(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.373(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(6) . ?
C33 C34 1.391(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.391(5) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C40 C41 1.407(5) . ?
C40 C46 1.399(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.369(6) . ?
C42 H42 0.9500 . ?
C42 C44 1.398(5) . ?
C44 C45 1.401(5) . ?
C45 H45 0.9500 . ?
C45 C46 1.378(6) . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.499(5) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 P1 S1 116.79(6) . . ?
O1 P1 S1 103.37(11) . . ?
O1 P1 S2 116.33(11) . . ?
O1 P1 C10 100.95(16) . . ?
C10 P1 S1 100.89(12) . . ?
C10 P1 S2 116.05(13) . . ?
S3 P2 S1 108.43(6) . . ?
O2 P2 S1 105.35(10) . . ?
O2 P2 S3 116.78(10) . . ?
O2 P2 C20 101.22(16) . . ?
C20 P2 S1 107.83(11) . . ?
C20 P2 S3 116.37(12) . . ?
P2 S1 P1 105.28(5) . . ?
C1 O1 P1 123.0(3) . . ?
C2 O2 P2 123.1(2) . . ?
C13 O3 C16 117.5(3) . . ?
C23 O4 C26 117.7(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 C2 110.7(3) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
O2 C2 C1 109.1(3) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C11 C10 P1 119.8(3) . . ?
C15 C10 P1 120.5(3) . . ?
C15 C10 C11 119.6(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
O3 C13 C12 115.8(4) . . ?
O3 C13 C14 123.4(4) . . ?
C14 C13 C12 120.8(3) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.1(4) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 120.6(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 121.7(3) . . ?
C25 C20 P2 119.4(3) . . ?
C25 C20 C21 118.8(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
O4 C23 C22 115.9(3) . . ?
O4 C23 C24 125.1(3) . . ?
C24 C23 C22 119.0(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
S5 P3 S4 115.81(6) . . ?
O5 P3 S4 104.08(11) . . ?
O5 P3 S5 116.58(11) . . ?
O5 P3 C30 101.06(16) . . ?
C30 P3 S4 99.97(12) . . ?
C30 P3 S5 116.87(13) . . ?
S6 P4 S4 108.16(6) . . ?
O6 P4 S4 105.68(10) . . ?
O6 P4 S6 116.04(11) . . ?
O6 P4 C40 100.89(16) . . ?
C40 P4 S4 108.06(12) . . ?
C40 P4 S6 117.18(13) . . ?
P4 S4 P3 104.19(5) . . ?
C50 O5 P3 123.2(3) . . ?
C51 O6 P4 125.0(2) . . ?
C33 O7 C36 117.7(3) . . ?
C44 O8 C47 117.6(3) . . ?
C31 C30 P3 119.7(3) . . ?
C35 C30 P3 121.0(3) . . ?
C35 C30 C31 119.2(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.6(3) . . ?
C33 C32 H32 119.7 . . ?
O7 C33 C32 115.8(3) . . ?
O7 C33 C34 124.0(4) . . ?
C32 C33 C34 120.2(3) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 C33 119.1(4) . . ?
C35 C34 H34 120.5 . . ?
C30 C35 H35 119.6 . . ?
C34 C35 C30 120.8(3) . . ?
C34 C35 H35 119.6 . . ?
O7 C36 H36A 109.5 . . ?
O7 C36 H36B 109.5 . . ?
O7 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C41 C40 P4 121.7(3) . . ?
C46 C40 P4 119.6(3) . . ?
C46 C40 C41 118.5(4) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.2(3) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C44 120.2(4) . . ?
C44 C42 H42 119.9 . . ?
O8 C44 C42 125.2(4) . . ?
O8 C44 C45 115.6(3) . . ?
C42 C44 C45 119.2(4) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 C44 120.5(3) . . ?
C46 C45 H45 119.7 . . ?
C40 C46 H46 119.8 . . ?
C45 C46 C40 120.5(3) . . ?
C45 C46 H46 119.8 . . ?
O8 C47 H47A 109.5 . . ?
O8 C47 H47B 109.5 . . ?
O8 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O5 C50 H50A 109.6 . . ?
O5 C50 H50B 109.6 . . ?
O5 C50 C51 110.3(3) . . ?
H50A C50 H50B 108.1 . . ?
C51 C50 H50A 109.6 . . ?
C51 C50 H50B 109.6 . . ?
O6 C51 C50 108.5(3) . . ?
O6 C51 H51A 110.0 . . ?
O6 C51 H51B 110.0 . . ?
C50 C51 H51A 110.0 . . ?
C50 C51 H51B 110.0 . . ?
H51A C51 H51B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 -80.6(4) . . . . ?
P1 C10 C11 C12 -174.7(3) . . . . ?
P1 C10 C15 C14 174.5(3) . . . . ?
P2 O2 C2 C1 -111.4(3) . . . . ?
P2 C20 C21 C22 177.3(3) . . . . ?
P2 C20 C25 C24 -176.7(3) . . . . ?
S1 P1 O1 C1 92.5(3) . . . . ?
S1 P1 C10 C11 -95.9(3) . . . . ?
S1 P1 C10 C15 87.6(3) . . . . ?
S1 P2 O2 C2 71.6(2) . . . . ?
S1 P2 C20 C21 31.6(3) . . . . ?
S1 P2 C20 C25 -151.4(3) . . . . ?
S2 P1 O1 C1 -36.9(3) . . . . ?
S2 P1 C10 C11 31.4(3) . . . . ?
S2 P1 C10 C15 -145.1(3) . . . . ?
S3 P2 O2 C2 -48.8(3) . . . . ?
S3 P2 C20 C21 153.6(3) . . . . ?
S3 P2 C20 C25 -29.4(3) . . . . ?
O1 P1 C10 C11 158.1(3) . . . . ?
O1 P1 C10 C15 -18.4(3) . . . . ?
O1 C1 C2 O2 71.6(4) . . . . ?
O2 P2 C20 C21 -78.7(3) . . . . ?
O2 P2 C20 C25 98.3(3) . . . . ?
O3 C13 C14 C15 -176.9(3) . . . . ?
O4 C23 C24 C25 -179.8(4) . . . . ?
C10 P1 O1 C1 -163.4(3) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C10 C15 C14 -2.0(6) . . . . ?
C11 C12 C13 O3 176.8(3) . . . . ?
C11 C12 C13 C14 -2.0(6) . . . . ?
C12 C13 C14 C15 1.9(6) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
C15 C10 C11 C12 1.8(6) . . . . ?
C16 O3 C13 C12 -178.3(4) . . . . ?
C16 O3 C13 C14 0.5(6) . . . . ?
C20 P2 O2 C2 -176.2(2) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C21 C20 C25 C24 0.5(6) . . . . ?
C21 C22 C23 O4 -179.6(3) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C25 1.1(6) . . . . ?
C23 C24 C25 C20 -1.1(6) . . . . ?
C25 C20 C21 C22 0.3(6) . . . . ?
C26 O4 C23 C22 -175.1(3) . . . . ?
C26 O4 C23 C24 5.7(6) . . . . ?
P3 O5 C50 C51 82.7(4) . . . . ?
P3 C30 C31 C32 176.1(3) . . . . ?
P3 C30 C35 C34 -176.2(3) . . . . ?
P4 O6 C51 C50 110.5(3) . . . . ?
P4 C40 C41 C42 -175.1(3) . . . . ?
P4 C40 C46 C45 174.8(3) . . . . ?
S4 P3 O5 C50 -95.5(3) . . . . ?
S4 P3 C30 C31 85.5(3) . . . . ?
S4 P3 C30 C35 -97.4(3) . . . . ?
S4 P4 O6 C51 -77.5(3) . . . . ?
S4 P4 C40 C41 -33.4(3) . . . . ?
S4 P4 C40 C46 152.5(3) . . . . ?
S5 P3 O5 C50 33.3(3) . . . . ?
S5 P3 C30 C31 -40.3(3) . . . . ?
S5 P3 C30 C35 136.8(3) . . . . ?
S6 P4 O6 C51 42.3(3) . . . . ?
S6 P4 C40 C41 -155.8(3) . . . . ?
S6 P4 C40 C46 30.1(3) . . . . ?
O5 P3 C30 C31 -167.9(3) . . . . ?
O5 P3 C30 C35 9.2(4) . . . . ?
O5 C50 C51 O6 -67.6(4) . . . . ?
O6 P4 C40 C41 77.3(3) . . . . ?
O6 P4 C40 C46 -96.9(3) . . . . ?
O7 C33 C34 C35 177.8(3) . . . . ?
O8 C44 C45 C46 -179.7(3) . . . . ?
C30 P3 O5 C50 161.1(3) . . . . ?
C30 C31 C32 C33 -0.2(6) . . . . ?
C31 C30 C35 C34 0.9(6) . . . . ?
C31 C32 C33 O7 -177.9(3) . . . . ?
C31 C32 C33 C34 1.5(6) . . . . ?
C32 C33 C34 C35 -1.6(6) . . . . ?
C33 C34 C35 C30 0.4(6) . . . . ?
C35 C30 C31 C32 -0.9(6) . . . . ?
C36 O7 C33 C32 173.9(4) . . . . ?
C36 O7 C33 C34 -5.5(5) . . . . ?
C40 P4 O6 C51 170.0(3) . . . . ?
C40 C41 C42 C44 1.3(6) . . . . ?
C41 C40 C46 C45 0.5(5) . . . . ?
C41 C42 C44 O8 179.3(4) . . . . ?
C41 C42 C44 C45 -1.1(6) . . . . ?
C42 C44 C45 C46 0.6(6) . . . . ?
C44 C45 C46 C40 -0.3(6) . . . . ?
C46 C40 C41 C42 -0.9(6) . . . . ?
C47 O8 C44 C42 -0.5(6) . . . . ?
C47 O8 C44 C45 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 719125'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-26 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 O6 P2 S4'
_chemical_formula_sum            'C20 H24 O6 P2 S4'
_chemical_formula_weight         550.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8942(8)
_cell_length_b                   9.3182(11)
_cell_length_c                   19.921(3)
_cell_angle_alpha                95.844(10)
_cell_angle_beta                 90.407(10)
_cell_angle_gamma                93.486(10)
_cell_volume                     1270.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3891
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      2.5185
_cell_measurement_theta_min      28.414
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.89065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7730
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'KM4CCD, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3746
_reflns_number_total             4687
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.372
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+1.2651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
2.c Me refined with riding coordinates:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.60568(13) 0.70015(9) 0.14420(4) 0.0258(2) Uani 1 1 d . . . . .
P2 P 0.86934(12) 0.71371(9) 0.35340(4) 0.0249(2) Uani 1 1 d . . . . .
S1 S 0.71040(12) 0.55195(8) 0.20758(4) 0.0262(2) Uani 1 1 d . . . . .
S2 S 0.95857(11) 0.65756(9) 0.25378(4) 0.0259(2) Uani 1 1 d . . . . .
S3 S 0.38090(14) 0.59302(10) 0.10123(5) 0.0378(3) Uani 1 1 d . . . . .
S4 S 1.10372(13) 0.80218(10) 0.39916(5) 0.0348(2) Uani 1 1 d . . . . .
O1 O 0.5709(3) 0.8472(2) 0.19034(12) 0.0278(5) Uani 1 1 d . . . . .
O2 O 0.6848(3) 0.8096(2) 0.35078(12) 0.0298(5) Uani 1 1 d . . . . .
O3 O 0.6431(4) 1.1958(3) 0.25980(15) 0.0451(7) Uani 1 1 d . . . . .
O4 O 0.3171(4) 1.1529(3) 0.25555(16) 0.0469(7) Uani 1 1 d . . . . .
O5 O 0.5364(4) 0.1795(2) 0.46183(13) 0.0357(6) Uani 1 1 d . . . . .
O6 O 1.3014(5) 0.8940(3) -0.00971(17) 0.0590(8) Uani 1 1 d . . . . .
C1 C 0.4267(5) 0.8529(3) 0.24346(18) 0.0286(8) Uani 1 1 d . . . . .
H1A H 0.413937 0.759649 0.263287 0.034 Uiso 1 1 calc R . . . .
H1B H 0.298398 0.872886 0.225063 0.034 Uiso 1 1 calc R . . . .
C2 C 0.4976(5) 0.9746(3) 0.29702(18) 0.0286(8) Uani 1 1 d . . . . .
H2 H 0.404680 0.975846 0.335371 0.034 Uiso 1 1 calc R . . . .
C3 C 0.6996(5) 0.9513(3) 0.32470(18) 0.0290(8) Uani 1 1 d . . . . .
H3A H 0.797083 0.952737 0.288482 0.035 Uiso 1 1 calc R . . . .
H3B H 0.738627 1.028017 0.361190 0.035 Uiso 1 1 calc R . . . .
C4 C 0.4988(5) 1.1211(4) 0.26903(18) 0.0315(8) Uani 1 1 d . . . . .
C5 C 0.2972(7) 1.2880(4) 0.2247(2) 0.0482(11) Uani 1 1 d . . . . .
H5A H 0.328996 1.372086 0.258288 0.058 Uiso 1 1 calc R . . . .
H5B H 0.387329 1.293202 0.186440 0.058 Uiso 1 1 calc R . . . .
C6 C 0.0985(7) 1.2895(5) 0.2013(3) 0.0629(14) Uani 1 1 d . . . . .
H6A H 0.081397 1.378782 0.180413 0.094 Uiso 1 1 calc R . . . .
H6B H 0.068708 1.206053 0.167951 0.094 Uiso 1 1 calc R . . . .
H6C H 0.010593 1.284641 0.239528 0.094 Uiso 1 1 calc R . . . .
C10 C 0.8035(5) 0.7606(4) 0.09399(18) 0.0307(8) Uani 1 1 d . . . . .
C11 C 0.9268(5) 0.8825(4) 0.1170(2) 0.0356(8) Uani 1 1 d . . . . .
H11 H 0.899267 0.938080 0.158133 0.043 Uiso 1 1 calc R . . . .
C12 C 1.0876(6) 0.9216(4) 0.0802(2) 0.0442(10) Uani 1 1 d . . . . .
H12 H 1.168895 1.003936 0.096488 0.053 Uiso 1 1 calc R . . . .
C13 C 1.1320(6) 0.8433(4) 0.0203(2) 0.0440(10) Uani 1 1 d . . . . .
C14 C 1.0114(7) 0.7247(5) -0.0039(2) 0.0485(11) Uani 1 1 d . . . . .
H14 H 1.039586 0.671357 -0.045545 0.058 Uiso 1 1 calc R . . . .
C15 C 0.8457(6) 0.6822(4) 0.0331(2) 0.0388(9) Uani 1 1 d . . . . .
H15 H 0.763956 0.600429 0.016403 0.047 Uiso 1 1 calc R . . . .
C16 C 1.3650(8) 0.8110(6) -0.0677(3) 0.0705(14) Uani 1 1 d . . . . .
H16A H 1.484491 0.857431 -0.083982 0.106 Uiso 1 1 calc R . . . .
H16B H 1.390436 0.713868 -0.056405 0.106 Uiso 1 1 calc R . . . .
H16C H 1.264153 0.803945 -0.103025 0.106 Uiso 1 1 calc R . . . .
C20 C 0.7585(5) 0.5563(3) 0.38599(16) 0.0252(7) Uani 1 1 d . . . . .
C21 C 0.8790(5) 0.4555(4) 0.4099(2) 0.0350(9) Uani 1 1 d . . . . .
H21 H 1.016174 0.472574 0.408720 0.042 Uiso 1 1 calc R . . . .
C22 C 0.8012(5) 0.3326(4) 0.4350(2) 0.0352(9) Uani 1 1 d . . . . .
H22 H 0.884511 0.265931 0.451252 0.042 Uiso 1 1 calc R . . . .
C23 C 0.5996(5) 0.3059(3) 0.43653(17) 0.0286(8) Uani 1 1 d . . . . .
C24 C 0.4778(5) 0.4051(4) 0.41373(19) 0.0317(8) Uani 1 1 d . . . . .
H24 H 0.340738 0.388149 0.415585 0.038 Uiso 1 1 calc R . . . .
C25 C 0.5568(5) 0.5289(4) 0.38827(18) 0.0301(8) Uani 1 1 d . . . . .
H25 H 0.473124 0.595598 0.372248 0.036 Uiso 1 1 calc R . . . .
C26 C 0.3290(5) 0.1517(4) 0.4689(2) 0.0372(9) Uani 1 1 d . . . . .
H26A H 0.303722 0.058835 0.487311 0.056 Uiso 1 1 calc R . . . .
H26B H 0.277795 0.228970 0.499536 0.056 Uiso 1 1 calc R . . . .
H26C H 0.265055 0.148357 0.424618 0.056 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.1180(12) . ?
P1 S3 1.9364(12) . ?
P1 O1 1.602(2) . ?
P1 C10 1.794(4) . ?
P2 S2 2.1060(13) . ?
P2 S4 1.9457(11) . ?
P2 O2 1.602(2) . ?
P2 C20 1.795(3) . ?
S1 S2 2.0811(11) . ?
O1 C1 1.456(4) . ?
O2 C3 1.465(4) . ?
O3 C4 1.206(4) . ?
O4 C4 1.336(4) . ?
O4 C5 1.468(4) . ?
O5 C23 1.376(4) . ?
O5 C26 1.449(4) . ?
O6 C13 1.395(5) . ?
O6 C16 1.411(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.530(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.530(5) . ?
C2 C4 1.526(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.446(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C10 C11 1.412(5) . ?
C10 C15 1.392(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(6) . ?
C13 C14 1.385(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.422(6) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.407(5) . ?
C20 C25 1.401(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(5) . ?
C23 C24 1.393(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(5) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S3 P1 S1 102.40(5) . . ?
O1 P1 S1 107.75(10) . . ?
O1 P1 S3 117.80(10) . . ?
O1 P1 C10 100.09(14) . . ?
C10 P1 S1 108.21(12) . . ?
C10 P1 S3 120.04(12) . . ?
S4 P2 S2 104.01(5) . . ?
O2 P2 S2 108.32(10) . . ?
O2 P2 S4 117.94(10) . . ?
O2 P2 C20 100.13(14) . . ?
C20 P2 S2 109.08(11) . . ?
C20 P2 S4 117.09(11) . . ?
S2 S1 P1 104.74(5) . . ?
S1 S2 P2 103.23(5) . . ?
C1 O1 P1 121.63(19) . . ?
C3 O2 P2 121.4(2) . . ?
C4 O4 C5 115.9(3) . . ?
C23 O5 C26 117.7(3) . . ?
C13 O6 C16 117.2(4) . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
O1 C1 C2 106.9(2) . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C1 C2 H2 108.0 . . ?
C3 C2 C1 112.1(3) . . ?
C3 C2 H2 108.0 . . ?
C4 C2 C1 110.9(3) . . ?
C4 C2 H2 108.0 . . ?
C4 C2 C3 109.8(3) . . ?
O2 C3 C2 106.1(3) . . ?
O2 C3 H3A 110.5 . . ?
O2 C3 H3B 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
O3 C4 O4 125.3(3) . . ?
O3 C4 C2 124.7(3) . . ?
O4 C4 C2 110.0(3) . . ?
O4 C5 H5A 110.1 . . ?
O4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 O4 107.9(3) . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C11 C10 P1 121.1(3) . . ?
C15 C10 P1 120.2(3) . . ?
C15 C10 C11 118.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 O6 114.3(4) . . ?
C12 C13 C14 119.3(4) . . ?
C14 C13 O6 126.4(4) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.9(4) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 118.7(3) . . ?
C25 C20 P2 122.8(3) . . ?
C25 C20 C21 118.5(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
O5 C23 C22 115.5(3) . . ?
O5 C23 C24 124.6(3) . . ?
C24 C23 C22 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.7(3) . . ?
C24 C25 H25 119.7 . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C1 C2 152.0(2) . . . . ?
P1 C10 C11 C12 175.1(3) . . . . ?
P1 C10 C15 C14 -175.3(3) . . . . ?
P2 O2 C3 C2 152.2(2) . . . . ?
P2 C20 C21 C22 -179.6(3) . . . . ?
P2 C20 C25 C24 179.7(3) . . . . ?
S1 P1 O1 C1 -64.0(2) . . . . ?
S1 P1 C10 C11 -89.1(3) . . . . ?
S1 P1 C10 C15 86.8(3) . . . . ?
S2 P2 O2 C3 -63.8(2) . . . . ?
S2 P2 C20 C21 79.9(3) . . . . ?
S2 P2 C20 C25 -99.7(3) . . . . ?
S3 P1 O1 C1 51.1(3) . . . . ?
S3 P1 C10 C11 154.1(2) . . . . ?
S3 P1 C10 C15 -30.1(3) . . . . ?
S4 P2 O2 C3 53.9(3) . . . . ?
S4 P2 C20 C21 -37.8(3) . . . . ?
S4 P2 C20 C25 142.6(3) . . . . ?
O1 P1 C10 C11 23.5(3) . . . . ?
O1 P1 C10 C15 -160.6(3) . . . . ?
O1 C1 C2 C3 -57.6(3) . . . . ?
O1 C1 C2 C4 65.6(3) . . . . ?
O2 P2 C20 C21 -166.5(3) . . . . ?
O2 P2 C20 C25 13.9(3) . . . . ?
O5 C23 C24 C25 -179.2(3) . . . . ?
O6 C13 C14 C15 178.0(4) . . . . ?
C1 C2 C3 O2 -56.6(3) . . . . ?
C1 C2 C4 O3 -113.0(4) . . . . ?
C1 C2 C4 O4 66.2(4) . . . . ?
C3 C2 C4 O3 11.4(5) . . . . ?
C3 C2 C4 O4 -169.4(3) . . . . ?
C4 O4 C5 C6 168.4(4) . . . . ?
C4 C2 C3 O2 179.6(3) . . . . ?
C5 O4 C4 O3 2.4(6) . . . . ?
C5 O4 C4 C2 -176.8(3) . . . . ?
C10 P1 O1 C1 -176.9(2) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C10 C15 C14 0.7(5) . . . . ?
C11 C12 C13 O6 -178.2(3) . . . . ?
C11 C12 C13 C14 1.1(6) . . . . ?
C12 C13 C14 C15 -1.2(6) . . . . ?
C13 C14 C15 C10 0.4(6) . . . . ?
C15 C10 C11 C12 -0.8(5) . . . . ?
C16 O6 C13 C12 174.2(4) . . . . ?
C16 O6 C13 C14 -5.0(6) . . . . ?
C20 P2 O2 C3 -177.9(2) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
C21 C20 C25 C24 0.2(5) . . . . ?
C21 C22 C23 O5 179.3(3) . . . . ?
C21 C22 C23 C24 -1.1(6) . . . . ?
C22 C23 C24 C25 1.3(5) . . . . ?
C23 C24 C25 C20 -0.8(5) . . . . ?
C25 C20 C21 C22 0.0(5) . . . . ?
C26 O5 C23 C22 175.8(3) . . . . ?
C26 O5 C23 C24 -3.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_comp_2b
_database_code_depnum_ccdc_archive 'CCDC 1560159'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 O4 P2 S4'
_chemical_formula_sum            'C19 H24 O4 P2 S4'
_chemical_formula_weight         506.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3171(12)
_cell_length_b                   9.1385(5)
_cell_length_c                   21.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.512(8)
_cell_angle_gamma                90
_cell_volume                     2397.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3266
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9945
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.600
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4046
_reflns_number_total             4378
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.9699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0682
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75473(3) 1.04420(4) 0.19294(2) 0.02316(9) Uani 1 1 d . . . . .
S2 S 0.86477(3) 0.88817(4) 0.16917(2) 0.02090(9) Uani 1 1 d . . . . .
S3 S 0.52581(3) 1.18352(4) 0.13708(2) 0.03189(11) Uani 1 1 d . . . . .
S4 S 0.93841(3) 0.55937(4) 0.20304(2) 0.02619(10) Uani 1 1 d . . . . .
P1 P 0.63516(3) 1.04879(4) 0.11438(2) 0.01959(9) Uani 1 1 d . . . . .
P2 P 0.83555(3) 0.70448(4) 0.22439(2) 0.01731(9) Uani 1 1 d . . . . .
O1 O 0.59860(8) 0.88545(11) 0.09970(5) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.70900(8) 0.66778(11) 0.21069(4) 0.0190(2) Uani 1 1 d . . . . .
O3 O 0.81600(9) 1.25011(12) -0.11410(5) 0.0297(2) Uani 1 1 d . . . . .
O4 O 0.85102(8) 0.85177(12) 0.49359(5) 0.0250(2) Uani 1 1 d . . . . .
C1 C 0.53035(11) 0.81212(16) 0.14130(7) 0.0207(3) Uani 1 1 d . . . . .
H1A H 0.452676 0.837629 0.129284 0.025 Uiso 1 1 calc R . . . .
H1B H 0.551035 0.844299 0.185128 0.025 Uiso 1 1 calc R . . . .
C2 C 0.54590(11) 0.64806(16) 0.13625(6) 0.0196(3) Uani 1 1 d . . . . .
C3 C 0.66636(11) 0.60793(15) 0.14999(6) 0.0193(3) Uani 1 1 d . . . . .
H3A H 0.674787 0.500185 0.150384 0.023 Uiso 1 1 calc R . . . .
H3B H 0.707632 0.648173 0.116860 0.023 Uiso 1 1 calc R . . . .
C4 C 0.50888(12) 0.59372(18) 0.06985(7) 0.0262(3) Uani 1 1 d . . . . .
H4A H 0.550054 0.644777 0.039928 0.039 Uiso 1 1 calc GR . . . .
H4B H 0.430679 0.613290 0.059512 0.039 Uiso 1 1 calc GR . . . .
H4C H 0.522148 0.488229 0.067528 0.039 Uiso 1 1 calc GR . . . .
C5 C 0.47848(13) 0.57698(17) 0.18382(7) 0.0264(3) Uani 1 1 d . . . . .
H5A H 0.486993 0.470446 0.182436 0.040 Uiso 1 1 calc GR . . . .
H5B H 0.401257 0.602432 0.173411 0.040 Uiso 1 1 calc GR . . . .
H5C H 0.504023 0.612555 0.226069 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.69854(11) 1.09538(16) 0.04645(7) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.73442(12) 1.23944(16) 0.04133(7) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.731357 1.305249 0.075389 0.028 Uiso 1 1 calc R . . . .
C12 C 0.77412(12) 1.28678(16) -0.01255(7) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.798200 1.384983 -0.015698 0.029 Uiso 1 1 calc R . . . .
C13 C 0.77898(11) 1.19044(17) -0.06257(7) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.74583(12) 1.04629(16) -0.05775(7) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.750830 0.980049 -0.091453 0.030 Uiso 1 1 calc R . . . .
C15 C 0.70517(12) 0.99933(16) -0.00318(7) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.681789 0.900862 0.000150 0.030 Uiso 1 1 calc R . . . .
C16 C 0.82329(15) 1.1577(2) -0.16730(8) 0.0341(4) Uani 1 1 d . . . . .
H16A H 0.853074 1.213586 -0.200466 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.750353 1.121409 -0.182865 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.871443 1.074727 -0.155012 0.051 Uiso 1 1 calc GR . . . .
C20 C 0.84243(11) 0.75595(15) 0.30484(6) 0.0180(3) Uani 1 1 d . . . . .
C21 C 0.94025(11) 0.73784(16) 0.34349(7) 0.0209(3) Uani 1 1 d . . . . .
H21 H 1.003160 0.703693 0.326084 0.025 Uiso 1 1 calc R . . . .
C22 C 0.94684(11) 0.76905(16) 0.40700(7) 0.0217(3) Uani 1 1 d . . . . .
H22 H 1.013636 0.755853 0.433218 0.026 Uiso 1 1 calc R . . . .
C23 C 0.85458(12) 0.81990(15) 0.43193(7) 0.0196(3) Uani 1 1 d . . . . .
C24 C 0.75678(12) 0.84111(16) 0.39333(7) 0.0226(3) Uani 1 1 d . . . . .
H24 H 0.694425 0.877687 0.410564 0.027 Uiso 1 1 calc R . . . .
C25 C 0.75062(11) 0.80917(16) 0.33047(7) 0.0218(3) Uani 1 1 d . . . . .
H25 H 0.683878 0.823215 0.304297 0.026 Uiso 1 1 calc R . . . .
C26 C 0.94732(13) 0.82220(19) 0.53573(7) 0.0304(4) Uani 1 1 d . . . . .
H26A H 1.008474 0.879607 0.523215 0.046 Uiso 1 1 calc GR . . . .
H26B H 0.964880 0.717750 0.534262 0.046 Uiso 1 1 calc GR . . . .
H26C H 0.934473 0.849016 0.578541 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0705(5) . ?
S1 P1 2.1081(6) . ?
S2 P2 2.1085(5) . ?
S3 P1 1.9276(5) . ?
S4 P2 1.9248(5) . ?
P1 O1 1.5804(10) . ?
P1 C10 1.7804(14) . ?
P2 O2 1.5888(10) . ?
P2 C20 1.7803(14) . ?
O1 C1 1.4564(16) . ?
O2 C3 1.4538(16) . ?
O3 C13 1.3564(18) . ?
O3 C16 1.430(2) . ?
O4 C23 1.3591(17) . ?
O4 C26 1.4329(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5168(19) . ?
C2 C3 1.5244(19) . ?
C2 C4 1.5277(19) . ?
C2 C5 1.5309(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C10 C11 1.397(2) . ?
C10 C15 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(2) . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.3926(19) . ?
C20 C25 1.399(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(2) . ?
C23 C24 1.396(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 S1 P1 103.57(2) . . ?
S1 S2 P2 104.58(2) . . ?
S3 P1 S1 104.83(2) . . ?
O1 P1 S1 107.33(4) . . ?
O1 P1 S3 117.52(4) . . ?
O1 P1 C10 101.79(6) . . ?
C10 P1 S1 109.08(5) . . ?
C10 P1 S3 115.94(5) . . ?
S4 P2 S2 104.84(2) . . ?
O2 P2 S2 106.90(4) . . ?
O2 P2 S4 117.97(4) . . ?
O2 P2 C20 99.95(6) . . ?
C20 P2 S2 109.95(5) . . ?
C20 P2 S4 116.87(5) . . ?
C1 O1 P1 118.94(9) . . ?
C3 O2 P2 119.48(8) . . ?
C13 O3 C16 117.99(12) . . ?
C23 O4 C26 117.20(11) . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
O1 C1 C2 108.96(11) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
C1 C2 C3 110.61(11) . . ?
C1 C2 C4 111.16(12) . . ?
C1 C2 C5 106.83(11) . . ?
C3 C2 C4 106.44(11) . . ?
C3 C2 C5 111.03(12) . . ?
C4 C2 C5 110.83(12) . . ?
O2 C3 C2 109.11(11) . . ?
O2 C3 H3A 109.9 . . ?
O2 C3 H3B 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C10 P1 117.49(11) . . ?
C15 C10 P1 123.02(11) . . ?
C15 C10 C11 119.26(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.57(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.88(14) . . ?
C13 C12 H12 120.1 . . ?
O3 C13 C12 114.86(13) . . ?
O3 C13 C14 124.87(14) . . ?
C14 C13 C12 120.26(14) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.52(14) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 120.48(14) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 119.21(11) . . ?
C21 C20 C25 119.40(13) . . ?
C25 C20 P2 121.35(10) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.73(13) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.21(13) . . ?
C23 C22 H22 120.4 . . ?
O4 C23 C22 124.32(13) . . ?
O4 C23 C24 115.22(13) . . ?
C22 C23 C24 120.46(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.04(13) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.15(13) . . ?
C24 C25 H25 119.9 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 P1 O1 C1 73.09(9) . . . . ?
S1 P1 C10 C11 -71.36(11) . . . . ?
S1 P1 C10 C15 114.20(12) . . . . ?
S2 P2 O2 C3 70.44(10) . . . . ?
S2 P2 C20 C21 -94.96(12) . . . . ?
S2 P2 C20 C25 87.38(12) . . . . ?
S3 P1 O1 C1 -44.61(10) . . . . ?
S3 P1 C10 C11 46.64(12) . . . . ?
S3 P1 C10 C15 -127.81(11) . . . . ?
S4 P2 O2 C3 -47.22(10) . . . . ?
S4 P2 C20 C21 24.34(13) . . . . ?
S4 P2 C20 C25 -153.32(10) . . . . ?
P1 O1 C1 C2 -155.82(9) . . . . ?
P1 C10 C11 C12 -173.53(11) . . . . ?
P1 C10 C15 C14 173.57(12) . . . . ?
P2 O2 C3 C2 -153.61(9) . . . . ?
P2 C20 C21 C22 -176.39(11) . . . . ?
P2 C20 C25 C24 176.72(12) . . . . ?
O1 P1 C10 C11 175.43(11) . . . . ?
O1 P1 C10 C15 0.98(14) . . . . ?
O1 C1 C2 C3 55.44(14) . . . . ?
O1 C1 C2 C4 -62.57(14) . . . . ?
O1 C1 C2 C5 176.39(11) . . . . ?
O2 P2 C20 C21 152.86(12) . . . . ?
O2 P2 C20 C25 -24.81(13) . . . . ?
O3 C13 C14 C15 -177.41(14) . . . . ?
O4 C23 C24 C25 -178.55(13) . . . . ?
C1 C2 C3 O2 54.37(15) . . . . ?
C4 C2 C3 O2 175.24(11) . . . . ?
C5 C2 C3 O2 -64.05(14) . . . . ?
C10 P1 O1 C1 -172.39(10) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C11 C12 C13 O3 177.86(13) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C12 C13 C14 C15 1.5(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C15 C10 C11 C12 1.1(2) . . . . ?
C16 O3 C13 C12 179.95(13) . . . . ?
C16 O3 C13 C14 -1.0(2) . . . . ?
C20 P2 O2 C3 -175.01(10) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C21 C20 C25 C24 -0.9(2) . . . . ?
C21 C22 C23 O4 178.91(14) . . . . ?
C21 C22 C23 C24 -0.8(2) . . . . ?
C22 C23 C24 C25 1.2(2) . . . . ?
C23 C24 C25 C20 -0.3(2) . . . . ?
C25 C20 C21 C22 1.3(2) . . . . ?
C26 O4 C23 C22 -3.9(2) . . . . ?
C26 O4 C23 C24 175.84(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a_cis
_database_code_depnum_ccdc_archive 'CCDC 1561560'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O4 P2 S3'
_chemical_formula_sum            'C16 H18 O4 P2 S3'
_chemical_formula_weight         432.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.284(6)
_cell_length_b                   21.511(6)
_cell_length_c                   8.717(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3803(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    107
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      4.75
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17031
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                6283
_reflns_number_total             8098
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-Red32'
_computing_data_collection       'STOE X-Area'
_computing_data_reduction        'STOE X-Red32'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         8098
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+4.9065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.89(13)
 0.11(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C51(H51A,H51B), C52(H52A,H52B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24),
 C25(H25), C31(H31), C32(H32), C34(H34), C35(H35), C41(H41), C42(H42), C44(H44),
  C45(H45)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C36(H36A,H36B,H36C), C46(H46A,H46B,
 H46C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.66948(7) 0.59865(7) 0.9604(2) 0.0207(3) Uani 1 1 d . . . . .
S2 S 0.62035(9) 0.56507(7) 0.6162(2) 0.0309(4) Uani 1 1 d . . . . .
S3 S 0.75070(10) 0.58923(8) 1.2748(2) 0.0302(4) Uani 1 1 d . . . . .
P1 P 0.68453(8) 0.61388(7) 0.7249(2) 0.0187(3) Uani 1 1 d . . . . .
P2 P 0.76098(8) 0.61686(7) 1.0664(2) 0.0210(4) Uani 1 1 d . . . . .
O1 O 0.7600(2) 0.5993(2) 0.6929(6) 0.0228(10) Uani 1 1 d . . . . .
O2 O 0.8152(2) 0.5828(2) 0.9644(6) 0.0268(10) Uani 1 1 d . . . . .
O3 O 0.7093(2) 0.88546(18) 0.6302(6) 0.0252(10) Uani 1 1 d . . . . .
O4 O 0.8074(3) 0.8866(2) 0.9914(7) 0.0353(12) Uani 1 1 d . . . . .
C1 C 0.7912(3) 0.5400(3) 0.7156(9) 0.0259(14) Uani 1 1 d . . . . .
H1A H 0.834212 0.539698 0.662004 0.031 Uiso 1 1 calc R . . . .
H1B H 0.763385 0.507051 0.669603 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8020(4) 0.5255(3) 0.8833(8) 0.0266(15) Uani 1 1 d . . . . .
H2A H 0.762300 0.505246 0.926493 0.032 Uiso 1 1 calc R . . . .
H2B H 0.839734 0.496726 0.895012 0.032 Uiso 1 1 calc R . . . .
C10 C 0.6868(3) 0.6961(3) 0.6951(8) 0.0203(14) Uani 1 1 d . . . . .
C11 C 0.6540(3) 0.7368(3) 0.7911(8) 0.0210(13) Uani 1 1 d . . . . .
H11 H 0.626929 0.720494 0.870353 0.025 Uiso 1 1 calc R . . . .
C12 C 0.6594(3) 0.8010(3) 0.7750(9) 0.0220(14) Uani 1 1 d . . . . .
H12 H 0.637505 0.828369 0.843552 0.026 Uiso 1 1 calc R . . . .
C13 C 0.6977(3) 0.8237(3) 0.6563(8) 0.0200(14) Uani 1 1 d . . . . .
C14 C 0.7287(3) 0.7836(3) 0.5538(9) 0.0242(14) Uani 1 1 d . . . . .
H14 H 0.753041 0.799943 0.469778 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7241(3) 0.7197(3) 0.5743(8) 0.0229(14) Uani 1 1 d . . . . .
H15 H 0.746303 0.692200 0.506388 0.027 Uiso 1 1 calc R . . . .
C16 C 0.6812(3) 0.9278(3) 0.7382(9) 0.0276(15) Uani 1 1 d . . . . .
H16A H 0.694165 0.970351 0.711672 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.697215 0.917784 0.841390 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.633069 0.924299 0.735720 0.041 Uiso 1 1 calc GR . . . .
C20 C 0.7812(3) 0.6968(3) 1.0410(8) 0.0218(14) Uani 1 1 d . . . . .
C21 C 0.7508(3) 0.7398(3) 1.1395(9) 0.0248(14) Uani 1 1 d . . . . .
H21 H 0.723004 0.725586 1.219809 0.030 Uiso 1 1 calc R . . . .
C22 C 0.7613(3) 0.8026(3) 1.1199(9) 0.0268(15) Uani 1 1 d . . . . .
H22 H 0.741118 0.831478 1.187543 0.032 Uiso 1 1 calc R . . . .
C23 C 0.8014(3) 0.8238(3) 1.0009(9) 0.0260(15) Uani 1 1 d . . . . .
C24 C 0.8320(3) 0.7819(3) 0.9039(9) 0.0272(15) Uani 1 1 d . . . . .
H24 H 0.860045 0.796230 0.824168 0.033 Uiso 1 1 calc R . . . .
C25 C 0.8212(3) 0.7183(3) 0.9241(9) 0.0268(16) Uani 1 1 d . . . . .
H25 H 0.841540 0.689437 0.856587 0.032 Uiso 1 1 calc R . . . .
C26 C 0.8469(4) 0.9120(4) 0.8707(11) 0.041(2) Uani 1 1 d . . . . .
H26A H 0.843433 0.957471 0.871711 0.061 Uiso 1 1 calc GR . . . .
H26B H 0.831378 0.896122 0.771719 0.061 Uiso 1 1 calc GR . . . .
H26C H 0.893038 0.899905 0.885873 0.061 Uiso 1 1 calc GR . . . .
S4 S 1.06093(7) 0.61950(7) 0.4693(2) 0.0200(3) Uani 1 1 d . . . . .
S5 S 0.97764(10) 0.60375(8) 0.7808(2) 0.0289(4) Uani 1 1 d . . . . .
S6 S 1.11344(8) 0.59221(7) 0.1261(2) 0.0277(4) Uani 1 1 d . . . . .
P3 P 0.96833(8) 0.63362(7) 0.5742(2) 0.0187(3) Uani 1 1 d . . . . .
P4 P 1.04646(8) 0.63772(7) 0.2352(2) 0.0177(3) Uani 1 1 d . . . . .
O5 O 0.9157(2) 0.6004(2) 0.4676(6) 0.0263(10) Uani 1 1 d . . . . .
O6 O 0.9720(2) 0.6204(2) 0.2003(5) 0.0211(10) Uani 1 1 d . . . . .
O7 O 0.9212(3) 0.9021(2) 0.4917(7) 0.0383(13) Uani 1 1 d . . . . .
O8 O 1.0188(2) 0.90815(19) 0.1247(7) 0.0291(11) Uani 1 1 d . . . . .
C30 C 0.9476(3) 0.7132(3) 0.5521(8) 0.0184(13) Uani 1 1 d . . . . .
C31 C 0.9789(3) 0.7571(3) 0.6454(8) 0.0223(14) Uani 1 1 d . . . . .
H31 H 1.007070 0.743527 0.725811 0.027 Uiso 1 1 calc R . . . .
C32 C 0.9693(3) 0.8199(3) 0.6219(9) 0.0269(15) Uani 1 1 d . . . . .
H32 H 0.991041 0.849399 0.685329 0.032 Uiso 1 1 calc R . . . .
C33 C 0.9280(3) 0.8397(3) 0.5062(9) 0.0276(16) Uani 1 1 d . . . . .
C34 C 0.8962(3) 0.7972(3) 0.4118(9) 0.0288(16) Uani 1 1 d . . . . .
H34 H 0.867799 0.811249 0.332434 0.035 Uiso 1 1 calc R . . . .
C35 C 0.9064(3) 0.7339(3) 0.4346(9) 0.0258(15) Uani 1 1 d . . . . .
H35 H 0.885184 0.704594 0.369700 0.031 Uiso 1 1 calc R . . . .
C36 C 0.8784(4) 0.9254(4) 0.3745(12) 0.049(2) Uani 1 1 d . . . . .
H36A H 0.880863 0.970905 0.372244 0.074 Uiso 1 1 calc GR . . . .
H36B H 0.833020 0.912550 0.396188 0.074 Uiso 1 1 calc GR . . . .
H36C H 0.892094 0.908733 0.274864 0.074 Uiso 1 1 calc GR . . . .
C40 C 1.0418(3) 0.7201(3) 0.2054(8) 0.0195(13) Uani 1 1 d . . . . .
C41 C 1.0735(3) 0.7620(3) 0.3020(8) 0.0212(14) Uani 1 1 d . . . . .
H41 H 1.099198 0.747218 0.385397 0.025 Uiso 1 1 calc R . . . .
C42 C 1.0675(3) 0.8255(3) 0.2766(9) 0.0240(14) Uani 1 1 d . . . . .
H42 H 1.089571 0.853939 0.342205 0.029 Uiso 1 1 calc R . . . .
C43 C 1.0301(3) 0.8472(3) 0.1580(8) 0.0224(15) Uani 1 1 d . . . . .
C44 C 0.9996(3) 0.8054(3) 0.0585(9) 0.0259(15) Uani 1 1 d . . . . .
H44 H 0.974957 0.820555 -0.026372 0.031 Uiso 1 1 calc R . . . .
C45 C 1.0049(3) 0.7422(3) 0.0824(8) 0.0236(14) Uani 1 1 d . . . . .
H45 H 0.983519 0.713915 0.015194 0.028 Uiso 1 1 calc R . . . .
C46 C 1.0458(4) 0.9538(3) 0.2270(10) 0.0324(16) Uani 1 1 d . . . . .
H46A H 1.035286 0.995502 0.189082 0.049 Uiso 1 1 calc GR . . . .
H46B H 1.093799 0.948769 0.232276 0.049 Uiso 1 1 calc GR . . . .
H46C H 1.026875 0.948232 0.329491 0.049 Uiso 1 1 calc GR . . . .
C51 C 0.9309(3) 0.5438(3) 0.3847(9) 0.0257(15) Uani 1 1 d . . . . .
H51A H 0.893421 0.514510 0.392264 0.031 Uiso 1 1 calc R . . . .
H51B H 0.970191 0.523707 0.430210 0.031 Uiso 1 1 calc R . . . .
C52 C 0.9440(3) 0.5591(3) 0.2185(9) 0.0248(14) Uani 1 1 d . . . . .
H52A H 0.974706 0.527923 0.175162 0.030 Uiso 1 1 calc R . . . .
H52B H 0.902183 0.556665 0.160267 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P1 2.101(3) . ?
S1 P2 2.110(2) . ?
S2 P1 1.922(2) . ?
S3 P2 1.922(3) . ?
P1 O1 1.587(5) . ?
P1 C10 1.789(6) . ?
P2 O2 1.592(5) . ?
P2 C20 1.782(7) . ?
O1 C1 1.439(7) . ?
O2 C2 1.446(8) . ?
O3 C13 1.368(7) . ?
O3 C16 1.428(8) . ?
O4 C23 1.360(8) . ?
O4 C26 1.432(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 C11 1.381(9) . ?
C10 C15 1.392(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(9) . ?
C13 C14 1.393(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(8) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C20 C21 1.404(9) . ?
C20 C25 1.381(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.395(10) . ?
C23 C24 1.383(10) . ?
C24 H24 0.9500 . ?
C24 C25 1.396(10) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
S4 P3 2.111(2) . ?
S4 P4 2.098(3) . ?
S5 P3 1.921(3) . ?
S6 P4 1.926(2) . ?
P3 O5 1.586(5) . ?
P3 C30 1.772(6) . ?
P4 O6 1.585(4) . ?
P4 C40 1.794(6) . ?
O5 C51 1.448(8) . ?
O6 C52 1.444(7) . ?
O7 C33 1.356(8) . ?
O7 C36 1.430(10) . ?
O8 C43 1.362(7) . ?
O8 C46 1.435(9) . ?
C30 C31 1.400(9) . ?
C30 C35 1.394(9) . ?
C31 H31 0.9500 . ?
C31 C32 1.381(9) . ?
C32 H32 0.9500 . ?
C32 C33 1.378(10) . ?
C33 C34 1.388(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.393(9) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C40 C41 1.391(9) . ?
C40 C45 1.391(9) . ?
C41 H41 0.9500 . ?
C41 C42 1.388(9) . ?
C42 H42 0.9500 . ?
C42 C43 1.365(10) . ?
C43 C44 1.394(10) . ?
C44 H44 0.9500 . ?
C44 C45 1.380(9) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 C52 1.509(10) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P1 S1 P2 105.74(10) . . ?
S2 P1 S1 107.34(11) . . ?
O1 P1 S1 106.3(2) . . ?
O1 P1 S2 117.3(2) . . ?
O1 P1 C10 98.3(3) . . ?
C10 P1 S1 107.4(2) . . ?
C10 P1 S2 119.1(2) . . ?
S3 P2 S1 105.14(11) . . ?
O2 P2 S1 106.1(2) . . ?
O2 P2 S3 117.4(2) . . ?
O2 P2 C20 102.4(3) . . ?
C20 P2 S1 109.1(2) . . ?
C20 P2 S3 116.2(2) . . ?
C1 O1 P1 125.1(4) . . ?
C2 O2 P2 122.5(4) . . ?
C13 O3 C16 116.2(5) . . ?
C23 O4 C26 118.3(6) . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
O1 C1 C2 112.3(5) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
O2 C2 C1 108.9(5) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C11 C10 P1 121.8(5) . . ?
C11 C10 C15 119.3(6) . . ?
C15 C10 P1 118.9(5) . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.0(6) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.1(6) . . ?
C13 C12 H12 121.0 . . ?
O3 C13 C12 124.4(6) . . ?
O3 C13 C14 114.7(6) . . ?
C12 C13 C14 121.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.6(6) . . ?
C14 C15 H15 120.2 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C20 P2 117.3(5) . . ?
C25 C20 P2 123.3(5) . . ?
C25 C20 C21 119.2(6) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(7) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(6) . . ?
C23 C22 H22 119.9 . . ?
O4 C23 C22 115.0(6) . . ?
O4 C23 C24 124.8(7) . . ?
C24 C23 C22 120.2(6) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(7) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 C24 120.8(7) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
P4 S4 P3 105.66(9) . . ?
S5 P3 S4 105.69(11) . . ?
O5 P3 S4 106.3(2) . . ?
O5 P3 S5 117.7(2) . . ?
O5 P3 C30 102.2(3) . . ?
C30 P3 S4 107.7(2) . . ?
C30 P3 S5 116.6(2) . . ?
S6 P4 S4 106.67(10) . . ?
O6 P4 S4 106.03(19) . . ?
O6 P4 S6 117.2(2) . . ?
O6 P4 C40 98.9(3) . . ?
C40 P4 S4 109.4(2) . . ?
C40 P4 S6 117.9(2) . . ?
C51 O5 P3 121.9(4) . . ?
C52 O6 P4 124.6(4) . . ?
C33 O7 C36 118.4(7) . . ?
C43 O8 C46 117.5(6) . . ?
C31 C30 P3 118.7(5) . . ?
C35 C30 P3 122.1(5) . . ?
C35 C30 C31 118.9(6) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.7(6) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.1 . . ?
C33 C32 C31 119.8(7) . . ?
C33 C32 H32 120.1 . . ?
O7 C33 C32 115.9(7) . . ?
O7 C33 C34 123.3(7) . . ?
C32 C33 C34 120.8(6) . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.4(7) . . ?
C35 C34 H34 120.3 . . ?
C30 C35 H35 119.8 . . ?
C34 C35 C30 120.4(6) . . ?
C34 C35 H35 119.8 . . ?
O7 C36 H36A 109.5 . . ?
O7 C36 H36B 109.5 . . ?
O7 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C41 C40 P4 121.9(5) . . ?
C45 C40 P4 118.5(5) . . ?
C45 C40 C41 119.6(6) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0(6) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.8 . . ?
C43 C42 C41 120.4(6) . . ?
C43 C42 H42 119.8 . . ?
O8 C43 C42 125.8(6) . . ?
O8 C43 C44 114.4(6) . . ?
C42 C43 C44 119.8(6) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.4(7) . . ?
C45 C44 H44 119.8 . . ?
C40 C45 H45 120.1 . . ?
C44 C45 C40 119.7(6) . . ?
C44 C45 H45 120.1 . . ?
O8 C46 H46A 109.5 . . ?
O8 C46 H46B 109.5 . . ?
O8 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O5 C51 H51A 109.8 . . ?
O5 C51 H51B 109.8 . . ?
O5 C51 C52 109.5(5) . . ?
H51A C51 H51B 108.2 . . ?
C52 C51 H51A 109.8 . . ?
C52 C51 H51B 109.8 . . ?
O6 C52 C51 111.9(5) . . ?
O6 C52 H52A 109.2 . . ?
O6 C52 H52B 109.2 . . ?
C51 C52 H52A 109.2 . . ?
C51 C52 H52B 109.2 . . ?
H52A C52 H52B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 P1 O1 C1 61.8(5) . . . . ?
S1 P1 C10 C11 -27.3(6) . . . . ?
S1 P1 C10 C15 150.9(5) . . . . ?
S1 P2 O2 C2 -32.5(6) . . . . ?
S1 P2 C20 C21 80.0(6) . . . . ?
S1 P2 C20 C25 -95.5(6) . . . . ?
S2 P1 O1 C1 -58.3(6) . . . . ?
S2 P1 C10 C11 94.8(6) . . . . ?
S2 P1 C10 C15 -86.9(5) . . . . ?
S3 P2 O2 C2 84.7(5) . . . . ?
S3 P2 C20 C21 -38.5(6) . . . . ?
S3 P2 C20 C25 146.0(5) . . . . ?
P1 O1 C1 C2 -74.0(7) . . . . ?
P1 C10 C11 C12 175.3(5) . . . . ?
P1 C10 C15 C14 -177.2(5) . . . . ?
P2 O2 C2 C1 102.4(6) . . . . ?
P2 C20 C21 C22 -176.1(5) . . . . ?
P2 C20 C25 C24 175.9(5) . . . . ?
O1 P1 C10 C11 -137.5(6) . . . . ?
O1 P1 C10 C15 40.8(6) . . . . ?
O1 C1 C2 O2 -33.3(8) . . . . ?
O2 P2 C20 C21 -167.9(5) . . . . ?
O2 P2 C20 C25 16.6(6) . . . . ?
O3 C13 C14 C15 175.9(6) . . . . ?
O4 C23 C24 C25 -179.1(7) . . . . ?
C10 P1 O1 C1 172.8(5) . . . . ?
C10 C11 C12 C13 1.7(10) . . . . ?
C11 C10 C15 C14 1.1(10) . . . . ?
C11 C12 C13 O3 -177.6(6) . . . . ?
C11 C12 C13 C14 1.4(10) . . . . ?
C12 C13 C14 C15 -3.2(10) . . . . ?
C13 C14 C15 C10 1.9(10) . . . . ?
C15 C10 C11 C12 -2.9(10) . . . . ?
C16 O3 C13 C12 2.4(9) . . . . ?
C16 O3 C13 C14 -176.6(6) . . . . ?
C20 P2 O2 C2 -146.8(5) . . . . ?
C20 C21 C22 C23 0.8(11) . . . . ?
C21 C20 C25 C24 0.5(10) . . . . ?
C21 C22 C23 O4 179.1(6) . . . . ?
C21 C22 C23 C24 -1.3(11) . . . . ?
C22 C23 C24 C25 1.4(11) . . . . ?
C23 C24 C25 C20 -1.0(11) . . . . ?
C25 C20 C21 C22 -0.4(10) . . . . ?
C26 O4 C23 C22 -179.0(7) . . . . ?
C26 O4 C23 C24 1.4(10) . . . . ?
S4 P3 O5 C51 34.1(5) . . . . ?
S4 P3 C30 C31 -76.1(5) . . . . ?
S4 P3 C30 C35 97.1(5) . . . . ?
S4 P4 O6 C52 -61.3(5) . . . . ?
S4 P4 C40 C41 27.8(6) . . . . ?
S4 P4 C40 C45 -151.7(5) . . . . ?
S5 P3 O5 C51 -84.0(5) . . . . ?
S5 P3 C30 C31 42.4(6) . . . . ?
S5 P3 C30 C35 -144.4(5) . . . . ?
S6 P4 O6 C52 57.6(5) . . . . ?
S6 P4 C40 C41 -94.3(6) . . . . ?
S6 P4 C40 C45 86.2(5) . . . . ?
P3 O5 C51 C52 -102.2(6) . . . . ?
P3 C30 C31 C32 173.4(5) . . . . ?
P3 C30 C35 C34 -173.8(5) . . . . ?
P4 O6 C52 C51 76.5(7) . . . . ?
P4 C40 C41 C42 -178.7(5) . . . . ?
P4 C40 C45 C44 178.9(5) . . . . ?
O5 P3 C30 C31 172.2(5) . . . . ?
O5 P3 C30 C35 -14.6(6) . . . . ?
O5 C51 C52 O6 30.6(7) . . . . ?
O6 P4 C40 C41 138.4(5) . . . . ?
O6 P4 C40 C45 -41.1(6) . . . . ?
O7 C33 C34 C35 179.7(6) . . . . ?
O8 C43 C44 C45 -177.6(6) . . . . ?
C30 P3 O5 C51 146.9(5) . . . . ?
C30 C31 C32 C33 0.5(10) . . . . ?
C31 C30 C35 C34 -0.6(10) . . . . ?
C31 C32 C33 O7 179.7(6) . . . . ?
C31 C32 C33 C34 -0.5(11) . . . . ?
C32 C33 C34 C35 -0.1(11) . . . . ?
C33 C34 C35 C30 0.7(11) . . . . ?
C35 C30 C31 C32 0.0(10) . . . . ?
C36 O7 C33 C32 -179.4(7) . . . . ?
C36 O7 C33 C34 0.8(10) . . . . ?
C40 P4 O6 C52 -174.6(5) . . . . ?
C40 C41 C42 C43 0.7(10) . . . . ?
C41 C40 C45 C44 -0.7(10) . . . . ?
C41 C42 C43 O8 177.8(6) . . . . ?
C41 C42 C43 C44 -2.3(10) . . . . ?
C42 C43 C44 C45 2.4(10) . . . . ?
C43 C44 C45 C40 -0.9(10) . . . . ?
C45 C40 C41 C42 0.8(10) . . . . ?
C46 O8 C43 C42 -3.2(10) . . . . ?
C46 O8 C43 C44 176.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.89(13)
2 0.11(13)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b_cis
_database_code_depnum_ccdc_archive 'CCDC 944068'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 O4 P2 S3'
_chemical_formula_sum            'C19 H24 O4 P2 S3'
_chemical_formula_weight         474.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2880(18)
_cell_length_b                   18.3863(13)
_cell_length_c                   12.2511(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.627(13)
_cell_angle_gamma                90
_cell_volume                     2346.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3058
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.78
_cell_measurement_theta_min      2.11
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
        (compiled Aug  3 2011,13:03:54)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11898
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'KM4CCD, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2318
_reflns_number_total             4297
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+1.4040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
2.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.90327(13) 0.16935(7) 0.13527(9) 0.0558(4) Uani 1 1 d . . . . .
P2 P 0.89331(13) 0.01360(7) 0.28717(10) 0.0564(4) Uani 1 1 d . . . . .
S1 S 0.79771(16) 0.22554(9) 0.00014(12) 0.0898(6) Uani 1 1 d . . . . .
S2 S 0.80813(12) 0.06950(7) 0.12287(10) 0.0594(4) Uani 1 1 d . . . . .
S3 S 0.78057(15) -0.06721(8) 0.27300(14) 0.0828(5) Uani 1 1 d . . . . .
O1 O 0.9251(3) 0.20147(16) 0.2610(2) 0.0564(8) Uani 1 1 d . . . . .
O2 O 1.4343(4) 0.1192(2) 0.1691(3) 0.0827(11) Uani 1 1 d . . . . .
O3 O 0.9107(3) 0.07238(16) 0.3852(2) 0.0571(8) Uani 1 1 d . . . . .
O4 O 1.4289(4) -0.0523(2) 0.3509(4) 0.0971(13) Uani 1 1 d . . . . .
C1 C 1.0638(5) 0.1519(2) 0.1495(3) 0.0509(11) Uani 1 1 d . . . . .
C2 C 1.1671(5) 0.1903(3) 0.2270(4) 0.0653(14) Uani 1 1 d . . . . .
H2 H 1.153906 0.224737 0.276761 0.078 Uiso 1 1 calc R . . . .
C3 C 1.2885(5) 0.1784(3) 0.2314(4) 0.0671(14) Uani 1 1 d . . . . .
H3 H 1.357126 0.204696 0.284058 0.081 Uiso 1 1 calc R . . . .
C4 C 1.3095(5) 0.1276(3) 0.1580(4) 0.0598(13) Uani 1 1 d . . . . .
C5 C 1.2082(5) 0.0894(3) 0.0795(4) 0.0669(14) Uani 1 1 d . . . . .
H5 H 1.221738 0.055324 0.029344 0.080 Uiso 1 1 calc R . . . .
C6 C 1.0861(5) 0.1017(3) 0.0754(4) 0.0602(13) Uani 1 1 d . . . . .
H6 H 1.017456 0.075930 0.021814 0.072 Uiso 1 1 calc R . . . .
C7 C 1.4591(6) 0.0658(4) 0.0965(6) 0.117(3) Uani 1 1 d . . . . .
H7A H 1.549184 0.065051 0.112168 0.175 Uiso 1 1 calc R . . . .
H7B H 1.432943 0.018924 0.113492 0.175 Uiso 1 1 calc R . . . .
H7C H 1.411779 0.077522 0.014796 0.175 Uiso 1 1 calc R . . . .
C8 C 1.0552(4) -0.0078(2) 0.3115(4) 0.0532(11) Uani 1 1 d . . . . .
C9 C 1.1584(5) 0.0360(3) 0.3800(4) 0.0623(13) Uani 1 1 d . . . . .
H9 H 1.143691 0.077034 0.417469 0.075 Uiso 1 1 calc R . . . .
C10 C 1.2806(5) 0.0188(3) 0.3921(4) 0.0694(14) Uani 1 1 d . . . . .
H10 H 1.348791 0.047823 0.438778 0.083 Uiso 1 1 calc R . . . .
C11 C 1.3037(5) -0.0413(3) 0.3355(5) 0.0676(14) Uani 1 1 d . . . . .
C12 C 1.2035(5) -0.0852(3) 0.2677(4) 0.0681(14) Uani 1 1 d . . . . .
H12 H 1.218711 -0.125793 0.229671 0.082 Uiso 1 1 calc R . . . .
C13 C 1.0795(5) -0.0682(3) 0.2566(4) 0.0621(13) Uani 1 1 d . . . . .
H13 H 1.011770 -0.098022 0.211511 0.074 Uiso 1 1 calc R . . . .
C14 C 1.4604(7) -0.1160(4) 0.3038(7) 0.124(3) Uani 1 1 d . . . . .
H14A H 1.550829 -0.116556 0.321037 0.185 Uiso 1 1 calc R . . . .
H14B H 1.437858 -0.157842 0.338471 0.185 Uiso 1 1 calc R . . . .
H14C H 1.413778 -0.116812 0.219648 0.185 Uiso 1 1 calc R . . . .
C15 C 0.8161(5) 0.2241(3) 0.2880(4) 0.0656(14) Uani 1 1 d . . . . .
H15A H 0.737476 0.208830 0.224384 0.079 Uiso 1 1 calc R . . . .
H15B H 0.815062 0.276709 0.292515 0.079 Uiso 1 1 calc R . . . .
C16 C 0.8198(5) 0.1922(3) 0.4039(4) 0.0584(12) Uani 1 1 d . . . . .
C17 C 0.8007(5) 0.1101(3) 0.3953(4) 0.0677(14) Uani 1 1 d . . . . .
H17A H 0.788547 0.092753 0.465009 0.081 Uiso 1 1 calc R . . . .
H17B H 0.723820 0.098721 0.326802 0.081 Uiso 1 1 calc R . . . .
C18 C 0.9449(5) 0.2116(3) 0.5058(4) 0.0805(17) Uani 1 1 d . . . . .
H18A H 0.945006 0.190962 0.577767 0.121 Uiso 1 1 calc R . . . .
H18B H 1.016000 0.192542 0.490136 0.121 Uiso 1 1 calc R . . . .
H18C H 0.952541 0.263534 0.513575 0.121 Uiso 1 1 calc R . . . .
C19 C 0.7044(6) 0.2232(3) 0.4247(5) 0.0897(19) Uani 1 1 d . . . . .
H19A H 0.703461 0.204302 0.497378 0.135 Uiso 1 1 calc R . . . .
H19B H 0.710608 0.275297 0.429308 0.135 Uiso 1 1 calc R . . . .
H19C H 0.626676 0.209519 0.360393 0.135 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 1.9261(18) . ?
P1 S2 2.1028(18) . ?
P1 O1 1.578(3) . ?
P1 C1 1.782(5) . ?
P2 S2 2.1314(17) . ?
P2 S3 1.9203(19) . ?
P2 O3 1.571(3) . ?
P2 C8 1.779(5) . ?
O1 C15 1.453(5) . ?
O2 C4 1.371(6) . ?
O2 C7 1.422(6) . ?
O3 C17 1.468(6) . ?
O4 C11 1.367(6) . ?
O4 C14 1.409(7) . ?
C1 C2 1.381(6) . ?
C1 C6 1.383(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 C5 1.371(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(6) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.400(6) . ?
C8 C13 1.379(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(7) . ?
C11 C12 1.377(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(7) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.521(6) . ?
C16 C17 1.523(6) . ?
C16 C18 1.524(7) . ?
C16 C19 1.531(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 P1 S2 106.04(9) . . ?
O1 P1 S1 116.81(14) . . ?
O1 P1 S2 106.31(13) . . ?
O1 P1 C1 101.59(18) . . ?
C1 P1 S1 116.77(15) . . ?
C1 P1 S2 108.75(16) . . ?
S3 P2 S2 104.20(8) . . ?
O3 P2 S2 105.58(13) . . ?
O3 P2 S3 118.99(14) . . ?
O3 P2 C8 101.9(2) . . ?
C8 P2 S2 109.03(15) . . ?
C8 P2 S3 116.49(17) . . ?
P1 S2 P2 108.69(7) . . ?
C15 O1 P1 120.1(3) . . ?
C4 O2 C7 117.2(4) . . ?
C17 O3 P2 121.9(3) . . ?
C11 O4 C14 118.4(5) . . ?
C2 C1 P1 122.2(4) . . ?
C2 C1 C6 118.3(5) . . ?
C6 C1 P1 119.4(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
O2 C4 C3 116.1(5) . . ?
C5 C4 O2 124.0(5) . . ?
C5 C4 C3 119.9(5) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P2 122.5(4) . . ?
C13 C8 P2 118.7(4) . . ?
C13 C8 C9 118.8(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
O4 C11 C10 115.6(5) . . ?
O4 C11 C12 124.2(5) . . ?
C12 C11 C10 120.1(5) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(5) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 121.0(5) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 H15A 109.1 . . ?
O1 C15 H15B 109.1 . . ?
O1 C15 C16 112.4(4) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 C17 111.4(4) . . ?
C15 C16 C18 111.0(4) . . ?
C15 C16 C19 107.0(4) . . ?
C17 C16 C19 105.9(5) . . ?
C18 C16 C17 110.5(4) . . ?
C18 C16 C19 110.9(4) . . ?
O3 C17 C16 111.9(4) . . ?
O3 C17 H17A 109.2 . . ?
O3 C17 H17B 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C15 C16 130.0(4) . . . . ?
P1 C1 C2 C3 -176.4(4) . . . . ?
P1 C1 C6 C5 176.7(4) . . . . ?
P2 O3 C17 C16 -130.4(3) . . . . ?
P2 C8 C9 C10 -177.3(4) . . . . ?
P2 C8 C13 C12 176.6(4) . . . . ?
S1 P1 O1 C15 51.4(3) . . . . ?
S1 P1 C1 C2 101.9(4) . . . . ?
S1 P1 C1 C6 -73.6(4) . . . . ?
S2 P1 O1 C15 -66.7(3) . . . . ?
S2 P1 C1 C2 -138.2(4) . . . . ?
S2 P1 C1 C6 46.3(4) . . . . ?
S2 P2 O3 C17 62.4(3) . . . . ?
S2 P2 C8 C9 95.9(4) . . . . ?
S2 P2 C8 C13 -81.2(4) . . . . ?
S3 P2 O3 C17 -54.1(3) . . . . ?
S3 P2 C8 C9 -146.6(3) . . . . ?
S3 P2 C8 C13 36.3(4) . . . . ?
O1 P1 C1 C2 -26.4(4) . . . . ?
O1 P1 C1 C6 158.1(3) . . . . ?
O1 C15 C16 C17 -67.6(6) . . . . ?
O1 C15 C16 C18 56.0(5) . . . . ?
O1 C15 C16 C19 177.1(4) . . . . ?
O2 C4 C5 C6 179.8(5) . . . . ?
O3 P2 C8 C9 -15.4(4) . . . . ?
O3 P2 C8 C13 167.5(3) . . . . ?
O4 C11 C12 C13 -178.9(5) . . . . ?
C1 P1 O1 C15 179.6(3) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C3 C4 O2 -179.7(5) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
C7 O2 C4 C3 178.5(5) . . . . ?
C7 O2 C4 C5 -1.9(8) . . . . ?
C8 P2 O3 C17 176.2(3) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C9 C8 C13 C12 -0.6(7) . . . . ?
C9 C10 C11 O4 178.2(5) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C10 C11 C12 C13 0.2(8) . . . . ?
C11 C12 C13 C8 0.6(7) . . . . ?
C13 C8 C9 C10 -0.2(7) . . . . ?
C14 O4 C11 C10 174.8(5) . . . . ?
C14 O4 C11 C12 -6.0(8) . . . . ?
C15 C16 C17 O3 68.9(5) . . . . ?
C18 C16 C17 O3 -55.1(5) . . . . ?
C19 C16 C17 O3 -175.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b_trans
_database_code_depnum_ccdc_archive 'CCDC 944069'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 O4 P2 S3'
_chemical_formula_sum            'C19 H24 O4 P2 S3'
_chemical_formula_weight         474.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   14.6528(5)
_cell_length_b                   9.1347(3)
_cell_length_c                   17.8598(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.073(4)
_cell_angle_gamma                90
_cell_volume                     2272.57(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.665
_cell_measurement_theta_min      2.225
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15538
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.230
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'KM4CCD, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.788
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                6588
_reflns_number_total             7935
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.8347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.95(12)
 0.05(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C34(H34A,H34B), C35(H35A,H35B)
3.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C29(H29), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.40852(13) 0.54433(19) 0.33756(11) 0.0511(4) Uani 1 1 d . . . . .
P2 P 0.50153(12) 0.47864(19) 0.18841(10) 0.0463(4) Uani 1 1 d . . . . .
S1 S 0.49801(12) 0.63435(18) 0.27534(10) 0.0507(4) Uani 1 1 d . . . . .
S2 S 0.28086(15) 0.4962(2) 0.27213(13) 0.0652(5) Uani 1 1 d . . . . .
S3 S 0.60954(14) 0.5333(3) 0.15558(12) 0.0672(5) Uani 1 1 d . . . . .
O1 O 0.4703(4) 0.4165(5) 0.3891(3) 0.0610(12) Uani 1 1 d . . . . .
O2 O 0.5059(3) 0.3245(5) 0.2315(3) 0.0546(11) Uani 1 1 d . . . . .
O3 O 0.4476(4) 1.0399(6) 0.5584(3) 0.0716(15) Uani 1 1 d . . . . .
O4 O 0.1287(4) 0.4570(7) -0.0656(4) 0.0828(18) Uani 1 1 d . . . . .
C1 C 0.4207(5) 0.6884(7) 0.4081(4) 0.0485(15) Uani 1 1 d . . . . .
C2 C 0.3473(5) 0.7884(8) 0.3992(4) 0.0597(18) Uani 1 1 d . . . . .
H2 H 0.290178 0.778068 0.358159 0.072 Uiso 1 1 calc R . . . .
C3 C 0.3589(5) 0.9040(9) 0.4515(5) 0.065(2) Uani 1 1 d . . . . .
H3 H 0.308991 0.970184 0.445816 0.078 Uiso 1 1 calc R . . . .
C4 C 0.4436(5) 0.9221(7) 0.5118(4) 0.0525(16) Uani 1 1 d . . . . .
C5 C 0.5166(5) 0.8205(8) 0.5216(4) 0.0559(17) Uani 1 1 d . . . . .
H5 H 0.573362 0.830339 0.562981 0.067 Uiso 1 1 calc R . . . .
C6 C 0.5049(5) 0.7054(7) 0.4701(4) 0.0526(16) Uani 1 1 d . . . . .
H6 H 0.554207 0.637721 0.476933 0.063 Uiso 1 1 calc R . . . .
C7 C 0.5320(7) 1.0600(10) 0.6233(5) 0.080(3) Uani 1 1 d . . . . .
H7A H 0.525725 1.147143 0.651335 0.119 Uiso 1 1 calc R . . . .
H7B H 0.540920 0.977176 0.657848 0.119 Uiso 1 1 calc R . . . .
H7C H 0.586421 1.069413 0.604470 0.119 Uiso 1 1 calc R . . . .
C8 C 0.3882(5) 0.4705(7) 0.1137(4) 0.0469(15) Uani 1 1 d . . . . .
C9 C 0.3632(6) 0.5833(9) 0.0597(4) 0.066(2) Uani 1 1 d . . . . .
H9 H 0.405394 0.661217 0.064180 0.079 Uiso 1 1 calc R . . . .
C10 C 0.2770(6) 0.5837(9) -0.0009(4) 0.067(2) Uani 1 1 d . . . . .
H10 H 0.261558 0.660994 -0.036557 0.080 Uiso 1 1 calc R . . . .
C11 C 0.2152(5) 0.4695(9) -0.0076(4) 0.0581(18) Uani 1 1 d . . . . .
C12 C 0.2383(6) 0.3557(9) 0.0466(5) 0.068(2) Uani 1 1 d . . . . .
H12 H 0.195431 0.278755 0.042083 0.081 Uiso 1 1 calc R . . . .
C13 C 0.3232(5) 0.3553(8) 0.1064(5) 0.0606(19) Uani 1 1 d . . . . .
H13 H 0.337789 0.278457 0.142336 0.073 Uiso 1 1 calc R . . . .
C14 C 0.1031(7) 0.5658(12) -0.1245(5) 0.087(3) Uani 1 1 d . . . . .
H14A H 0.041192 0.543514 -0.160937 0.131 Uiso 1 1 calc R . . . .
H14B H 0.100774 0.659287 -0.100619 0.131 Uiso 1 1 calc R . . . .
H14C H 0.149919 0.568488 -0.151976 0.131 Uiso 1 1 calc R . . . .
C15 C 0.4588(6) 0.2631(7) 0.3676(5) 0.0635(19) Uani 1 1 d . . . . .
H15A H 0.407101 0.252362 0.318494 0.076 Uiso 1 1 calc R . . . .
H15B H 0.441429 0.208979 0.407924 0.076 Uiso 1 1 calc R . . . .
C16 C 0.5497(6) 0.2000(8) 0.3584(4) 0.0624(19) Uani 1 1 d . . . . .
C17 C 0.5848(5) 0.2911(8) 0.3018(4) 0.0587(18) Uani 1 1 d . . . . .
H17A H 0.612854 0.381472 0.327309 0.070 Uiso 1 1 calc R . . . .
H17B H 0.634131 0.237758 0.287379 0.070 Uiso 1 1 calc R . . . .
C18 C 0.6323(7) 0.1977(11) 0.4362(5) 0.091(3) Uani 1 1 d . . . . .
H18A H 0.688452 0.156791 0.427445 0.136 Uiso 1 1 calc R . . . .
H18B H 0.645712 0.295737 0.455848 0.136 Uiso 1 1 calc R . . . .
H18C H 0.614271 0.139054 0.473946 0.136 Uiso 1 1 calc R . . . .
C19 C 0.5260(7) 0.0424(8) 0.3257(6) 0.077(2) Uani 1 1 d . . . . .
H19A H 0.582465 -0.001536 0.318962 0.116 Uiso 1 1 calc R . . . .
H19B H 0.504475 -0.014902 0.362023 0.116 Uiso 1 1 calc R . . . .
H19C H 0.476339 0.046047 0.275796 0.116 Uiso 1 1 calc R . . . .
P3 P 0.98316(13) 1.05522(19) 0.46744(10) 0.0494(4) Uani 1 1 d . . . . .
P4 P 0.88362(12) 0.99321(18) 0.27303(10) 0.0448(4) Uani 1 1 d . . . . .
S4 S 0.88838(12) 1.14751(18) 0.36170(10) 0.0495(4) Uani 1 1 d . . . . .
S5 S 1.10935(15) 1.0096(2) 0.46471(13) 0.0641(5) Uani 1 1 d . . . . .
S6 S 0.77303(14) 1.0432(3) 0.18590(12) 0.0705(6) Uani 1 1 d . . . . .
O5 O 0.9233(4) 0.9262(5) 0.4884(3) 0.0580(12) Uani 1 1 d . . . . .
O6 O 0.8833(3) 0.8379(5) 0.3135(3) 0.0552(12) Uani 1 1 d . . . . .
O7 O 0.9358(4) 1.5387(6) 0.6721(3) 0.0685(14) Uani 1 1 d . . . . .
O8 O 1.2410(4) 1.0236(7) 0.1854(4) 0.0820(17) Uani 1 1 d . . . . .
C20 C 0.9704(5) 1.1968(7) 0.5331(4) 0.0480(15) Uani 1 1 d . . . . .
C21 C 0.8900(5) 1.1998(8) 0.5584(4) 0.0546(17) Uani 1 1 d . . . . .
H21 H 0.845704 1.123809 0.544397 0.066 Uiso 1 1 calc R . . . .
C22 C 0.8746(5) 1.3134(8) 0.6040(4) 0.0543(17) Uani 1 1 d . . . . .
H22 H 0.819484 1.315934 0.619351 0.065 Uiso 1 1 calc R . . . .
C23 C 0.9434(5) 1.4249(7) 0.6266(4) 0.0518(16) Uani 1 1 d . . . . .
C24 C 1.0245(5) 1.4206(7) 0.6027(4) 0.0544(17) Uani 1 1 d . . . . .
H24 H 1.070374 1.494174 0.618410 0.065 Uiso 1 1 calc R . . . .
C25 C 1.0379(5) 1.3076(7) 0.5555(4) 0.0510(15) Uani 1 1 d . . . . .
H25 H 1.092086 1.306072 0.538930 0.061 Uiso 1 1 calc R . . . .
C26 C 0.8493(7) 1.5503(10) 0.6929(6) 0.079(2) Uani 1 1 d . . . . .
H26A H 0.852593 1.635406 0.725205 0.118 Uiso 1 1 calc R . . . .
H26B H 0.795463 1.558872 0.645958 0.118 Uiso 1 1 calc R . . . .
H26C H 0.841934 1.464570 0.721540 0.118 Uiso 1 1 calc R . . . .
C27 C 0.9959(5) 0.9942(7) 0.2533(4) 0.0484(16) Uani 1 1 d . . . . .
C28 C 1.0517(5) 0.8705(7) 0.2568(4) 0.0534(16) Uani 1 1 d . . . . .
H28 H 1.034173 0.783065 0.275210 0.064 Uiso 1 1 calc R . . . .
C29 C 1.1321(5) 0.8751(8) 0.2335(4) 0.0581(18) Uani 1 1 d . . . . .
H29 H 1.167441 0.790103 0.234587 0.070 Uiso 1 1 calc R . . . .
C30 C 1.1616(6) 1.0060(8) 0.2081(5) 0.0592(18) Uani 1 1 d . . . . .
C31 C 1.1068(7) 1.1305(9) 0.2058(6) 0.087(3) Uani 1 1 d . . . . .
H31 H 1.125384 1.219333 0.189663 0.104 Uiso 1 1 calc R . . . .
C32 C 1.0263(7) 1.1226(9) 0.2272(6) 0.076(2) Uani 1 1 d . . . . .
H32 H 0.989602 1.206770 0.224196 0.092 Uiso 1 1 calc R . . . .
C33 C 1.2877(7) 0.8987(12) 0.1695(5) 0.086(3) Uani 1 1 d . . . . .
H33A H 1.342294 0.927901 0.154179 0.128 Uiso 1 1 calc R . . . .
H33B H 1.308501 0.838708 0.215784 0.128 Uiso 1 1 calc R . . . .
H33C H 1.244099 0.844124 0.127462 0.128 Uiso 1 1 calc R . . . .
C34 C 0.9334(5) 0.7721(7) 0.4723(4) 0.0599(19) Uani 1 1 d . . . . .
H34A H 0.952401 0.717990 0.521430 0.072 Uiso 1 1 calc R . . . .
H34B H 0.983409 0.760603 0.447671 0.072 Uiso 1 1 calc R . . . .
C35 C 0.8030(5) 0.8036(8) 0.3437(4) 0.0561(17) Uani 1 1 d . . . . .
H35A H 0.753665 0.750716 0.304057 0.067 Uiso 1 1 calc R . . . .
H35B H 0.775199 0.893559 0.355642 0.067 Uiso 1 1 calc R . . . .
C36 C 0.8396(5) 0.7103(7) 0.4183(4) 0.0567(18) Uani 1 1 d . . . . .
C37 C 0.8589(6) 0.5532(8) 0.3972(5) 0.071(2) Uani 1 1 d . . . . .
H37A H 0.800679 0.511405 0.363069 0.106 Uiso 1 1 calc R . . . .
H37B H 0.906905 0.553845 0.370891 0.106 Uiso 1 1 calc R . . . .
H37C H 0.881081 0.495816 0.444432 0.106 Uiso 1 1 calc R . . . .
C38 C 0.7604(7) 0.7134(11) 0.4573(6) 0.086(3) Uani 1 1 d . . . . .
H38A H 0.702358 0.673702 0.421770 0.129 Uiso 1 1 calc R . . . .
H38B H 0.779614 0.655798 0.504601 0.129 Uiso 1 1 calc R . . . .
H38C H 0.749314 0.812539 0.470068 0.129 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.129(3) . ?
P1 S2 1.924(3) . ?
P1 O1 1.585(5) . ?
P1 C1 1.793(7) . ?
P2 S1 2.118(2) . ?
P2 S3 1.917(3) . ?
P2 O2 1.596(4) . ?
P2 C8 1.780(7) . ?
O1 C15 1.449(8) . ?
O2 C17 1.452(8) . ?
O3 C4 1.350(8) . ?
O3 C7 1.420(10) . ?
O4 C11 1.370(9) . ?
O4 C14 1.410(11) . ?
C1 C2 1.383(9) . ?
C1 C6 1.387(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(10) . ?
C4 C5 1.385(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(9) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.381(10) . ?
C8 C13 1.398(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(11) . ?
C11 C12 1.389(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(10) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.507(11) . ?
C16 C17 1.517(11) . ?
C16 C18 1.534(11) . ?
C16 C19 1.552(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
P3 S4 2.140(2) . ?
P3 S5 1.911(3) . ?
P3 O5 1.582(5) . ?
P3 C20 1.795(7) . ?
P4 S4 2.105(2) . ?
P4 S6 1.921(2) . ?
P4 O6 1.593(5) . ?
P4 C27 1.786(7) . ?
O5 C34 1.453(8) . ?
O6 C35 1.472(8) . ?
O7 C23 1.345(8) . ?
O7 C26 1.431(10) . ?
O8 C30 1.355(9) . ?
O8 C33 1.404(11) . ?
C20 C21 1.386(10) . ?
C20 C25 1.385(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.401(9) . ?
C23 C24 1.383(10) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(9) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.385(9) . ?
C27 C32 1.385(10) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(10) . ?
C29 H29 0.9300 . ?
C29 C30 1.394(11) . ?
C30 C31 1.387(11) . ?
C31 H31 0.9300 . ?
C31 C32 1.349(12) . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C36 1.522(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.531(10) . ?
C36 C37 1.532(10) . ?
C36 C38 1.529(11) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 P1 S1 114.29(12) . . ?
O1 P1 S1 104.8(2) . . ?
O1 P1 S2 117.2(2) . . ?
O1 P1 C1 102.6(3) . . ?
C1 P1 S1 98.0(2) . . ?
C1 P1 S2 117.5(2) . . ?
S3 P2 S1 105.03(11) . . ?
O2 P2 S1 104.2(2) . . ?
O2 P2 S3 117.6(2) . . ?
O2 P2 C8 102.3(3) . . ?
C8 P2 S1 110.4(2) . . ?
C8 P2 S3 116.7(2) . . ?
P2 S1 P1 106.39(10) . . ?
C15 O1 P1 124.0(5) . . ?
C17 O2 P2 120.3(4) . . ?
C4 O3 C7 117.8(6) . . ?
C11 O4 C14 118.3(7) . . ?
C2 C1 P1 120.0(5) . . ?
C2 C1 C6 119.1(6) . . ?
C6 C1 P1 120.9(5) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(7) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(7) . . ?
C4 C3 H3 119.6 . . ?
O3 C4 C3 115.7(6) . . ?
O3 C4 C5 124.9(6) . . ?
C3 C4 C5 119.4(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(6) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(6) . . ?
C5 C6 H6 119.5 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P2 118.4(5) . . ?
C9 C8 C13 118.1(6) . . ?
C13 C8 P2 123.4(5) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.9(7) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.1(7) . . ?
C11 C10 H10 120.4 . . ?
O4 C11 C12 115.7(7) . . ?
C10 C11 O4 124.3(7) . . ?
C10 C11 C12 120.0(7) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(7) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0(7) . . ?
C12 C13 H13 120.0 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 H15A 109.3 . . ?
O1 C15 H15B 109.3 . . ?
O1 C15 C16 111.4(6) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 C17 111.0(6) . . ?
C15 C16 C18 112.4(7) . . ?
C15 C16 C19 107.1(7) . . ?
C17 C16 C18 106.0(7) . . ?
C17 C16 C19 109.9(6) . . ?
C18 C16 C19 110.5(7) . . ?
O2 C17 C16 110.3(6) . . ?
O2 C17 H17A 109.6 . . ?
O2 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S5 P3 S4 115.57(12) . . ?
O5 P3 S4 104.27(19) . . ?
O5 P3 S5 117.1(2) . . ?
O5 P3 C20 101.8(3) . . ?
C20 P3 S4 97.0(2) . . ?
C20 P3 S5 118.2(2) . . ?
S6 P4 S4 105.84(11) . . ?
O6 P4 S4 105.0(2) . . ?
O6 P4 S6 117.3(2) . . ?
O6 P4 C27 103.1(3) . . ?
C27 P4 S4 109.1(2) . . ?
C27 P4 S6 115.9(2) . . ?
P4 S4 P3 105.14(9) . . ?
C34 O5 P3 125.2(5) . . ?
C35 O6 P4 118.1(4) . . ?
C23 O7 C26 117.4(6) . . ?
C30 O8 C33 118.8(7) . . ?
C21 C20 P3 119.9(5) . . ?
C25 C20 P3 120.4(5) . . ?
C25 C20 C21 119.7(6) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.2(6) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(7) . . ?
C23 C22 H22 120.6 . . ?
O7 C23 C22 123.3(7) . . ?
O7 C23 C24 116.6(6) . . ?
C24 C23 C22 120.1(6) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.4(6) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.8(7) . . ?
C24 C25 H25 120.1 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 P4 123.6(5) . . ?
C28 C27 C32 117.3(7) . . ?
C32 C27 P4 118.8(5) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 120.9(7) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(7) . . ?
C30 C29 H29 119.7 . . ?
O8 C30 C29 125.5(7) . . ?
O8 C30 C31 115.9(7) . . ?
C31 C30 C29 118.5(8) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.8(8) . . ?
C32 C31 H31 120.1 . . ?
C27 C32 H32 118.6 . . ?
C31 C32 C27 122.7(7) . . ?
C31 C32 H32 118.6 . . ?
O8 C33 H33A 109.5 . . ?
O8 C33 H33B 109.5 . . ?
O8 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O5 C34 H34A 109.5 . . ?
O5 C34 H34B 109.5 . . ?
O5 C34 C36 110.9(6) . . ?
H34A C34 H34B 108.0 . . ?
C36 C34 H34A 109.5 . . ?
C36 C34 H34B 109.5 . . ?
O6 C35 H35A 109.8 . . ?
O6 C35 H35B 109.8 . . ?
O6 C35 C36 109.5(5) . . ?
H35A C35 H35B 108.2 . . ?
C36 C35 H35A 109.8 . . ?
C36 C35 H35B 109.8 . . ?
C34 C36 C35 110.4(6) . . ?
C34 C36 C37 107.7(6) . . ?
C34 C36 C38 111.6(7) . . ?
C35 C36 C37 110.4(6) . . ?
C38 C36 C35 106.0(6) . . ?
C38 C36 C37 110.7(7) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O1 C15 C16 119.3(6) . . . . ?
P1 C1 C2 C3 -176.7(6) . . . . ?
P1 C1 C6 C5 176.2(5) . . . . ?
P2 O2 C17 C16 144.4(5) . . . . ?
P2 C8 C9 C10 178.9(7) . . . . ?
P2 C8 C13 C12 -178.8(6) . . . . ?
S1 P1 O1 C15 -99.4(5) . . . . ?
S1 P1 C1 C2 103.4(6) . . . . ?
S1 P1 C1 C6 -73.8(6) . . . . ?
S1 P2 O2 C17 -59.7(5) . . . . ?
S1 P2 C8 C9 74.8(6) . . . . ?
S1 P2 C8 C13 -105.7(6) . . . . ?
S2 P1 O1 C15 28.4(6) . . . . ?
S2 P1 C1 C2 -19.4(7) . . . . ?
S2 P1 C1 C6 163.4(5) . . . . ?
S3 P2 O2 C17 56.1(5) . . . . ?
S3 P2 C8 C9 -44.9(6) . . . . ?
S3 P2 C8 C13 134.6(6) . . . . ?
O1 P1 C1 C2 -149.5(6) . . . . ?
O1 P1 C1 C6 33.4(6) . . . . ?
O1 C15 C16 C17 -53.3(8) . . . . ?
O1 C15 C16 C18 65.3(8) . . . . ?
O1 C15 C16 C19 -173.3(6) . . . . ?
O2 P2 C8 C9 -174.8(6) . . . . ?
O2 P2 C8 C13 4.8(7) . . . . ?
O3 C4 C5 C6 -179.4(7) . . . . ?
O4 C11 C12 C13 179.3(7) . . . . ?
C1 P1 O1 C15 158.6(6) . . . . ?
C1 C2 C3 C4 1.0(12) . . . . ?
C2 C1 C6 C5 -1.0(11) . . . . ?
C2 C3 C4 O3 178.8(7) . . . . ?
C2 C3 C4 C5 -2.1(12) . . . . ?
C3 C4 C5 C6 1.7(11) . . . . ?
C4 C5 C6 C1 -0.1(11) . . . . ?
C6 C1 C2 C3 0.5(11) . . . . ?
C7 O3 C4 C3 177.6(8) . . . . ?
C7 O3 C4 C5 -1.4(11) . . . . ?
C8 P2 O2 C17 -174.7(5) . . . . ?
C8 C9 C10 C11 -0.2(13) . . . . ?
C9 C8 C13 C12 0.8(11) . . . . ?
C9 C10 C11 O4 -179.2(7) . . . . ?
C9 C10 C11 C12 1.0(13) . . . . ?
C10 C11 C12 C13 -0.9(12) . . . . ?
C11 C12 C13 C8 0.0(12) . . . . ?
C13 C8 C9 C10 -0.7(12) . . . . ?
C14 O4 C11 C10 3.0(12) . . . . ?
C14 O4 C11 C12 -177.2(7) . . . . ?
C15 C16 C17 O2 -46.4(8) . . . . ?
C18 C16 C17 O2 -168.7(6) . . . . ?
C19 C16 C17 O2 71.9(8) . . . . ?
P3 O5 C34 C36 -119.8(6) . . . . ?
P3 C20 C21 C22 -174.9(5) . . . . ?
P3 C20 C25 C24 176.4(5) . . . . ?
P4 O6 C35 C36 -145.4(5) . . . . ?
P4 C27 C28 C29 173.4(5) . . . . ?
P4 C27 C32 C31 -175.4(8) . . . . ?
S4 P3 O5 C34 100.4(5) . . . . ?
S4 P3 C20 C21 78.9(5) . . . . ?
S4 P3 C20 C25 -97.7(5) . . . . ?
S4 P4 O6 C35 61.1(5) . . . . ?
S4 P4 C27 C28 124.9(6) . . . . ?
S4 P4 C27 C32 -60.3(7) . . . . ?
S5 P3 O5 C34 -28.7(6) . . . . ?
S5 P3 C20 C21 -157.1(5) . . . . ?
S5 P3 C20 C25 26.3(6) . . . . ?
S6 P4 O6 C35 -56.0(5) . . . . ?
S6 P4 C27 C28 -115.8(6) . . . . ?
S6 P4 C27 C32 59.0(7) . . . . ?
O5 P3 C20 C21 -27.3(6) . . . . ?
O5 P3 C20 C25 156.1(5) . . . . ?
O5 C34 C36 C35 53.5(8) . . . . ?
O5 C34 C36 C37 174.1(6) . . . . ?
O5 C34 C36 C38 -64.1(8) . . . . ?
O6 P4 C27 C28 13.7(7) . . . . ?
O6 P4 C27 C32 -171.5(6) . . . . ?
O6 C35 C36 C34 44.5(8) . . . . ?
O6 C35 C36 C37 -74.5(7) . . . . ?
O6 C35 C36 C38 165.6(6) . . . . ?
O7 C23 C24 C25 -179.8(6) . . . . ?
O8 C30 C31 C32 179.7(9) . . . . ?
C20 P3 O5 C34 -159.1(5) . . . . ?
C20 C21 C22 C23 -1.9(10) . . . . ?
C21 C20 C25 C24 -0.2(10) . . . . ?
C21 C22 C23 O7 -178.7(7) . . . . ?
C21 C22 C23 C24 0.6(10) . . . . ?
C22 C23 C24 C25 0.8(10) . . . . ?
C23 C24 C25 C20 -1.0(10) . . . . ?
C25 C20 C21 C22 1.7(10) . . . . ?
C26 O7 C23 C22 -4.8(11) . . . . ?
C26 O7 C23 C24 175.8(7) . . . . ?
C27 P4 O6 C35 175.4(5) . . . . ?
C27 C28 C29 C30 2.2(11) . . . . ?
C28 C27 C32 C31 -0.3(14) . . . . ?
C28 C29 C30 O8 178.5(7) . . . . ?
C28 C29 C30 C31 -1.1(12) . . . . ?
C29 C30 C31 C32 -0.7(15) . . . . ?
C30 C31 C32 C27 1.4(16) . . . . ?
C32 C27 C28 C29 -1.5(11) . . . . ?
C33 O8 C30 C29 14.5(12) . . . . ?
C33 O8 C30 C31 -166.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.95(12)
2 0.05(12)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3c_cis
_database_code_depnum_ccdc_archive 'CCDC 1558054'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 O4 P2 S3'
_chemical_formula_sum            'C18 H22 O4 P2 S3'
_chemical_formula_weight         460.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7882(11)
_cell_length_b                   8.8878(10)
_cell_length_c                   14.120(2)
_cell_angle_alpha                73.295(11)
_cell_angle_beta                 75.044(11)
_cell_angle_gamma                81.888(9)
_cell_volume                     1017.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14738
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.271
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3596
_reflns_number_total             5492
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.493
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1145P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.96919(10) 0.63175(9) 0.19138(6) 0.01883(19) Uani 1 1 d . . . . .
P2 P 0.81886(10) 0.28730(9) 0.35129(6) 0.01790(19) Uani 1 1 d . . . . .
S1 S 0.78352(9) 0.47949(9) 0.22911(6) 0.01908(18) Uani 1 1 d . . . . .
S2 S 0.91519(11) 0.81217(9) 0.08874(7) 0.0269(2) Uani 1 1 d . . . . .
S3 S 0.63105(10) 0.17189(10) 0.39217(6) 0.0236(2) Uani 1 1 d . . . . .
O1 O 0.9846(3) 0.6580(3) 0.29477(17) 0.0242(5) Uani 1 1 d . . . . .
O2 O 0.8571(3) 0.3557(3) 0.43387(16) 0.0224(5) Uani 1 1 d . . . . .
O3 O 1.5380(3) 0.2384(3) 0.05652(18) 0.0263(5) Uani 1 1 d . . . . .
O4 O 1.3925(3) -0.1241(3) 0.24938(18) 0.0277(5) Uani 1 1 d . . . . .
C1 C 0.8788(5) 0.7739(4) 0.3406(3) 0.0302(8) Uani 1 1 d . . . . .
H1A H 0.848948 0.861712 0.285643 0.036 Uiso 1 1 calc R . . . .
H1B H 0.937340 0.817522 0.376743 0.036 Uiso 1 1 calc R . . . .
C2 C 0.7332(5) 0.7117(5) 0.4126(3) 0.0352(9) Uani 1 1 d . . . . .
H2A H 0.672917 0.672739 0.375230 0.042 Uiso 1 1 calc R . . . .
H2B H 0.667869 0.800255 0.435865 0.042 Uiso 1 1 calc R . . . .
C3 C 0.7539(5) 0.5809(5) 0.5055(3) 0.0360(9) Uani 1 1 d . . . . .
H3A H 0.861432 0.583370 0.514596 0.043 Uiso 1 1 calc R . . . .
H3B H 0.678615 0.606816 0.565139 0.043 Uiso 1 1 calc R . . . .
C4 C 0.7326(5) 0.4132(4) 0.5092(3) 0.0286(8) Uani 1 1 d . . . . .
H4A H 0.734808 0.344447 0.577861 0.034 Uiso 1 1 calc R . . . .
H4B H 0.628459 0.408213 0.495880 0.034 Uiso 1 1 calc R . . . .
C10 C 1.1491(4) 0.5223(4) 0.1539(2) 0.0203(6) Uani 1 1 d . . . . .
C11 C 1.1827(4) 0.4953(4) 0.0577(2) 0.0209(6) Uani 1 1 d . . . . .
H11 H 1.114411 0.541639 0.013084 0.025 Uiso 1 1 calc R . . . .
C12 C 1.3148(4) 0.4015(4) 0.0273(2) 0.0228(6) Uani 1 1 d . . . . .
H12 H 1.337472 0.383428 -0.038206 0.027 Uiso 1 1 calc R . . . .
C13 C 1.4145(4) 0.3333(4) 0.0925(2) 0.0208(6) Uani 1 1 d . . . . .
C14 C 1.3847(4) 0.3621(4) 0.1877(2) 0.0218(6) Uani 1 1 d . . . . .
H14 H 1.455199 0.318782 0.231278 0.026 Uiso 1 1 calc R . . . .
C15 C 1.2505(4) 0.4550(4) 0.2180(2) 0.0225(6) Uani 1 1 d . . . . .
H15 H 1.227641 0.472863 0.283592 0.027 Uiso 1 1 calc R . . . .
C16 C 1.6501(4) 0.1724(4) 0.1178(3) 0.0288(7) Uani 1 1 d . . . . .
H16A H 1.738248 0.116323 0.080273 0.043 Uiso 1 1 calc GR . . . .
H16B H 1.598972 0.098800 0.180599 0.043 Uiso 1 1 calc GR . . . .
H16C H 1.689856 0.256998 0.134449 0.043 Uiso 1 1 calc GR . . . .
C20 C 0.9993(4) 0.1777(3) 0.3145(2) 0.0187(6) Uani 1 1 d . . . . .
C21 C 1.0372(4) 0.1408(4) 0.2210(2) 0.0204(6) Uani 1 1 d . . . . .
H21 H 0.972283 0.184567 0.173968 0.025 Uiso 1 1 calc R . . . .
C22 C 1.1694(4) 0.0406(4) 0.1959(2) 0.0206(6) Uani 1 1 d . . . . .
H22 H 1.194785 0.016778 0.131956 0.025 Uiso 1 1 calc R . . . .
C23 C 1.2636(4) -0.0241(3) 0.2651(2) 0.0213(6) Uani 1 1 d . . . . .
C24 C 1.2280(4) 0.0130(4) 0.3581(2) 0.0237(7) Uani 1 1 d . . . . .
H24 H 1.293684 -0.030378 0.404729 0.028 Uiso 1 1 calc R . . . .
C25 C 1.0970(4) 0.1128(4) 0.3829(2) 0.0222(6) Uani 1 1 d . . . . .
H25 H 1.073136 0.137555 0.446497 0.027 Uiso 1 1 calc R . . . .
C26 C 1.4357(5) -0.1637(4) 0.1535(3) 0.0314(8) Uani 1 1 d . . . . .
H26A H 1.455387 -0.067480 0.098060 0.047 Uiso 1 1 calc GR . . . .
H26B H 1.349605 -0.215464 0.146194 0.047 Uiso 1 1 calc GR . . . .
H26C H 1.531587 -0.235114 0.150823 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.1301(12) . ?
P1 S2 1.9237(12) . ?
P1 O1 1.584(2) . ?
P1 C10 1.776(3) . ?
P2 S1 2.1031(11) . ?
P2 S3 1.9379(12) . ?
P2 O2 1.584(2) . ?
P2 C20 1.779(3) . ?
O1 C1 1.465(4) . ?
O2 C4 1.464(4) . ?
O3 C13 1.360(4) . ?
O3 C16 1.431(4) . ?
O4 C23 1.350(4) . ?
O4 C26 1.440(4) . ?
C1 C2 1.477(5) . ?
C2 C3 1.515(6) . ?
C3 C4 1.513(5) . ?
C10 C11 1.397(4) . ?
C10 C15 1.387(5) . ?
C11 C12 1.379(4) . ?
C12 C13 1.389(5) . ?
C13 C14 1.393(4) . ?
C14 C15 1.387(4) . ?
C20 C21 1.397(4) . ?
C20 C25 1.404(5) . ?
C21 C22 1.394(4) . ?
C22 C23 1.390(5) . ?
C23 C24 1.393(4) . ?
C24 C25 1.384(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 P1 S1 105.45(5) . . ?
O1 P1 S1 106.64(10) . . ?
O1 P1 S2 118.28(10) . . ?
O1 P1 C10 102.69(14) . . ?
C10 P1 S1 107.31(11) . . ?
C10 P1 S2 115.78(11) . . ?
S3 P2 S1 105.77(5) . . ?
O2 P2 S1 107.38(10) . . ?
O2 P2 S3 116.82(10) . . ?
O2 P2 C20 101.48(14) . . ?
C20 P2 S1 109.87(11) . . ?
C20 P2 S3 115.26(11) . . ?
P2 S1 P1 108.77(5) . . ?
C1 O1 P1 121.1(2) . . ?
C4 O2 P2 122.1(2) . . ?
C13 O3 C16 117.7(3) . . ?
C23 O4 C26 117.3(3) . . ?
O1 C1 C2 114.7(3) . . ?
C1 C2 C3 116.7(4) . . ?
C4 C3 C2 119.2(3) . . ?
O2 C4 C3 111.2(3) . . ?
C11 C10 P1 117.5(3) . . ?
C15 C10 P1 123.0(2) . . ?
C15 C10 C11 119.4(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 120.0(3) . . ?
O3 C13 C12 115.3(3) . . ?
O3 C13 C14 124.2(3) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 118.9(3) . . ?
C14 C15 C10 121.0(3) . . ?
C21 C20 P2 120.2(2) . . ?
C21 C20 C25 118.9(3) . . ?
C25 C20 P2 120.6(2) . . ?
C22 C21 C20 120.8(3) . . ?
C23 C22 C21 119.5(3) . . ?
O4 C23 C22 124.5(3) . . ?
O4 C23 C24 115.2(3) . . ?
C22 C23 C24 120.3(3) . . ?
C25 C24 C23 120.2(3) . . ?
C24 C25 C20 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z590_pl
_database_code_depnum_ccdc_archive 'CCDC 1940750'
loop_
_audit_author_name
_audit_author_address
'Jaroslaw Chojnacki'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-07-15 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O4 P2 S3'
_chemical_formula_sum            'C16 H18 O4 P2 S3'
_chemical_formula_weight         432.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.284(4)
_cell_length_b                   21.511(6)
_cell_length_c                   8.717(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3803(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    107
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.64
_cell_measurement_theta_min      4.75
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16036
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.790
_reflns_Friedel_fraction_max     0.756
_reflns_number_gt                5977
_reflns_number_total             7658
_reflns_special_details          
'Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. Completness statistics refer to single and composite reflections containing twin component 1 only.'
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7658
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+2.0808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.80(11)
 0.20(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C27(H27A,H27B), C28(H28A,H28B)
3.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C15(H15), C16(H16),
 C9(H9), C10(H10), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16947(6) 0.09863(6) 0.71858(18) 0.0206(3) Uani 1 1 d . . . . .
S4 S 0.25075(9) 0.08922(7) 1.03293(19) 0.0300(3) Uani 1 1 d . . . . .
S5 S 0.12029(8) 0.06510(6) 0.3744(2) 0.0311(3) Uani 1 1 d . . . . .
P2 P 0.18451(7) 0.11387(6) 0.48317(18) 0.0188(3) Uani 1 1 d . . . . .
P3 P 0.26097(7) 0.11688(6) 0.82462(18) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.20938(19) 0.38543(15) 0.3883(5) 0.0254(9) Uani 1 1 d . . . . .
O3 O 0.3072(2) 0.38660(17) 0.7497(6) 0.0352(11) Uani 1 1 d . . . . .
O8 O 0.25984(19) 0.09942(17) 0.4511(5) 0.0228(9) Uani 1 1 d . . . . .
O9 O 0.31522(17) 0.08270(17) 0.7227(5) 0.0266(9) Uani 1 1 d . . . . .
C1 C 0.1868(2) 0.1960(2) 0.4535(7) 0.0202(12) Uani 1 1 d . . . . .
C0AA C 0.2508(3) 0.2397(2) 0.8977(8) 0.0257(12) Uani 1 1 d . . . . .
H0AA H 0.222974 0.225557 0.978065 0.031 Uiso 1 1 calc R . . . .
C2 C 0.1541(3) 0.2368(2) 0.5493(7) 0.0208(11) Uani 1 1 d . . . . .
H2 H 0.127128 0.220433 0.628688 0.025 Uiso 1 1 calc R . . . .
C3 C 0.1592(3) 0.3010(2) 0.5335(7) 0.0222(12) Uani 1 1 d . . . . .
H3 H 0.137143 0.328315 0.601966 0.027 Uiso 1 1 calc R . . . .
C4 C 0.1977(3) 0.3238(2) 0.4146(7) 0.0197(12) Uani 1 1 d . . . . .
C5 C 0.2288(3) 0.2836(2) 0.3120(7) 0.0242(12) Uani 1 1 d . . . . .
H5 H 0.253315 0.299850 0.228254 0.029 Uiso 1 1 calc R . . . .
C6 C 0.2240(3) 0.2198(2) 0.3325(7) 0.0235(12) Uani 1 1 d . . . . .
H6 H 0.245932 0.192390 0.264041 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1813(3) 0.4279(2) 0.4961(8) 0.0273(13) Uani 1 1 d . . . . .
H7A H 0.196602 0.417466 0.599596 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.133124 0.424953 0.492151 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.194944 0.470336 0.470493 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.2612(3) 0.3025(2) 0.8779(8) 0.0272(13) Uani 1 1 d . . . . .
H13 H 0.240960 0.331505 0.945387 0.033 Uiso 1 1 calc R . . . .
C14 C 0.3016(3) 0.3237(3) 0.7588(8) 0.0258(13) Uani 1 1 d . . . . .
C15 C 0.3319(3) 0.2818(3) 0.6617(8) 0.0262(13) Uani 1 1 d . . . . .
H15 H 0.359807 0.296111 0.581713 0.031 Uiso 1 1 calc R . . . .
C16 C 0.3211(3) 0.2186(3) 0.6821(7) 0.0266(13) Uani 1 1 d . . . . .
H16 H 0.341473 0.189693 0.614642 0.032 Uiso 1 1 calc R . . . .
C17 C 0.2809(3) 0.1969(2) 0.7998(7) 0.0214(12) Uani 1 1 d . . . . .
C18 C 0.3470(3) 0.4119(3) 0.6287(10) 0.0418(18) Uani 1 1 d . . . . .
H18A H 0.393242 0.400876 0.646084 0.063 Uiso 1 1 calc GR . . . .
H18B H 0.342372 0.457223 0.627165 0.063 Uiso 1 1 calc GR . . . .
H18C H 0.332430 0.394777 0.530094 0.063 Uiso 1 1 calc GR . . . .
C31 C 0.3020(3) 0.0253(2) 0.6417(7) 0.0270(13) Uani 1 1 d . . . . .
H31A H 0.262291 0.005007 0.684998 0.032 Uiso 1 1 calc R . . . .
H31B H 0.339709 -0.003512 0.653132 0.032 Uiso 1 1 calc R . . . .
C32 C 0.2910(3) 0.0399(2) 0.4741(8) 0.0259(12) Uani 1 1 d . . . . .
H32A H 0.334017 0.039574 0.420359 0.031 Uiso 1 1 calc R . . . .
H32B H 0.263150 0.007046 0.428113 0.031 Uiso 1 1 calc R . . . .
S3 S -0.02241(8) 0.39623(7) 0.53909(19) 0.0288(3) Uani 1 1 d . . . . .
S6 S 0.11340(7) 0.40779(6) -0.1157(2) 0.0278(3) Uani 1 1 d . . . . .
S7 S 0.06098(6) 0.38052(6) 0.22753(18) 0.0200(3) Uani 1 1 d . . . . .
P4 P -0.03167(7) 0.36640(6) 0.33247(17) 0.0188(3) Uani 1 1 d . . . . .
P5 P 0.04647(7) 0.36231(6) -0.00647(17) 0.0177(3) Uani 1 1 d . . . . .
O4 O -0.0787(2) 0.09786(18) 0.2498(6) 0.0384(11) Uani 1 1 d . . . . .
O10 O 0.01876(19) 0.09190(16) -0.1171(6) 0.0285(9) Uani 1 1 d . . . . .
O11 O -0.02804(18) 0.37957(17) -0.0418(5) 0.0218(9) Uani 1 1 d . . . . .
O12 O -0.08427(18) 0.39972(17) 0.2264(5) 0.0261(9) Uani 1 1 d . . . . .
C8 C 0.0301(3) 0.1529(2) -0.0840(7) 0.0221(12) Uani 1 1 d . . . . .
C9 C -0.0006(3) 0.1944(2) -0.1833(7) 0.0257(13) Uani 1 1 d . . . . .
H9 H -0.025571 0.179250 -0.267560 0.031 Uiso 1 1 calc R . . . .
C10 C 0.0050(3) 0.2578(2) -0.1596(7) 0.0239(12) Uani 1 1 d . . . . .
H10 H -0.016198 0.286160 -0.227078 0.029 Uiso 1 1 calc R . . . .
C11 C 0.0418(2) 0.2799(2) -0.0362(7) 0.0195(11) Uani 1 1 d . . . . .
C19 C -0.1216(4) 0.0746(3) 0.1326(10) 0.049(2) Uani 1 1 d . . . . .
H19A H -0.119597 0.029062 0.131079 0.073 Uiso 1 1 calc GR . . . .
H19B H -0.107651 0.090855 0.032695 0.073 Uiso 1 1 calc GR . . . .
H19C H -0.166906 0.087889 0.153688 0.073 Uiso 1 1 calc GR . . . .
C20 C -0.0523(2) 0.2869(2) 0.3103(7) 0.0180(11) Uani 1 1 d . . . . .
C21 C -0.0936(3) 0.2659(3) 0.1929(7) 0.0270(13) Uani 1 1 d . . . . .
H21 H -0.114952 0.295200 0.128186 0.032 Uiso 1 1 calc R . . . .
C22 C -0.1037(3) 0.2028(3) 0.1699(8) 0.0292(14) Uani 1 1 d . . . . .
H22 H -0.131910 0.188857 0.090067 0.035 Uiso 1 1 calc R . . . .
C23 C -0.0721(3) 0.1603(3) 0.2647(8) 0.0281(14) Uani 1 1 d . . . . .
C24 C -0.0307(3) 0.1800(2) 0.3806(8) 0.0262(12) Uani 1 1 d . . . . .
H24 H -0.009041 0.150519 0.444133 0.031 Uiso 1 1 calc R . . . .
C25 C -0.0211(3) 0.2428(2) 0.4035(7) 0.0217(12) Uani 1 1 d . . . . .
H25 H 0.007134 0.256379 0.483802 0.026 Uiso 1 1 calc R . . . .
C27 C -0.0693(3) 0.4564(2) 0.1430(7) 0.0262(13) Uani 1 1 d . . . . .
H27A H -0.030130 0.476727 0.188668 0.031 Uiso 1 1 calc R . . . .
H27B H -0.106913 0.485533 0.150328 0.031 Uiso 1 1 calc R . . . .
C28 C -0.0559(3) 0.4410(2) -0.0236(7) 0.0254(12) Uani 1 1 d . . . . .
H28A H -0.097624 0.443609 -0.082103 0.030 Uiso 1 1 calc R . . . .
H28B H -0.025029 0.472115 -0.066552 0.030 Uiso 1 1 calc R . . . .
C29 C 0.0676(3) 0.1746(2) 0.0349(7) 0.0242(12) Uani 1 1 d . . . . .
H29 H 0.089725 0.146085 0.100474 0.029 Uiso 1 1 calc R . . . .
C30 C 0.0735(3) 0.2379(2) 0.0601(7) 0.0215(12) Uani 1 1 d . . . . .
H30 H 0.099213 0.252720 0.143509 0.026 Uiso 1 1 calc R . . . .
C33 C 0.0457(3) 0.0462(2) -0.0153(8) 0.0315(14) Uani 1 1 d . . . . .
H33A H 0.035266 0.004513 -0.053864 0.047 Uiso 1 1 calc GR . . . .
H33B H 0.026577 0.051469 0.087092 0.047 Uiso 1 1 calc GR . . . .
H33C H 0.093639 0.051241 -0.009617 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 P2 2.100(3) . ?
S1 P3 2.110(2) . ?
S4 P3 1.922(3) . ?
S5 P2 1.922(2) . ?
P2 O8 1.584(4) . ?
P2 C1 1.787(5) . ?
P3 O9 1.594(4) . ?
P3 C17 1.781(5) . ?
O1 C4 1.366(6) . ?
O1 C7 1.429(7) . ?
O3 C14 1.360(6) . ?
O3 C18 1.436(8) . ?
O8 C32 1.442(6) . ?
O9 C31 1.448(7) . ?
C1 C2 1.381(8) . ?
C1 C6 1.394(8) . ?
C0AA H0AA 0.9500 . ?
C0AA C13 1.378(7) . ?
C0AA C17 1.397(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(8) . ?
C4 C5 1.396(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.398(9) . ?
C14 C15 1.380(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(8) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.511(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
S3 P4 1.921(3) . ?
S6 P5 1.926(2) . ?
S7 P4 2.112(2) . ?
S7 P5 2.098(3) . ?
P4 O12 1.583(4) . ?
P4 C20 1.772(5) . ?
P5 O11 1.586(4) . ?
P5 C11 1.794(5) . ?
O4 C19 1.433(8) . ?
O4 C23 1.356(6) . ?
O10 C8 1.363(6) . ?
O10 C33 1.433(7) . ?
O11 C28 1.446(6) . ?
O12 C27 1.451(7) . ?
C8 C9 1.392(8) . ?
C8 C29 1.367(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(8) . ?
C11 C30 1.390(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.397(8) . ?
C20 C25 1.400(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(9) . ?
C23 C24 1.380(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(7) . ?
C25 H25 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.514(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29 0.9500 . ?
C29 C30 1.386(7) . ?
C30 H30 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
P2 S1 P3 105.74(8) . . ?
S5 P2 S1 107.34(9) . . ?
O8 P2 S1 106.37(17) . . ?
O8 P2 S5 117.36(17) . . ?
O8 P2 C1 98.2(2) . . ?
C1 P2 S1 107.4(2) . . ?
C1 P2 S5 119.10(19) . . ?
S4 P3 S1 105.16(10) . . ?
O9 P3 S1 106.09(17) . . ?
O9 P3 S4 117.27(18) . . ?
O9 P3 C17 102.8(2) . . ?
C17 P3 S1 109.06(19) . . ?
C17 P3 S4 116.0(2) . . ?
C4 O1 C7 116.1(4) . . ?
C14 O3 C18 117.8(5) . . ?
C32 O8 P2 124.9(4) . . ?
C31 O9 P3 122.5(4) . . ?
C2 C1 P2 121.9(4) . . ?
C2 C1 C6 119.0(5) . . ?
C6 C1 P2 119.2(4) . . ?
C13 C0AA H0AA 119.9 . . ?
C13 C0AA C17 120.2(6) . . ?
C17 C0AA H0AA 119.9 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.3(5) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.9(5) . . ?
C4 C3 H3 121.1 . . ?
O1 C4 C3 124.5(5) . . ?
O1 C4 C5 114.6(5) . . ?
C3 C4 C5 120.9(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 H6 120.0 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C0AA C13 H13 120.0 . . ?
C0AA C13 C14 120.1(6) . . ?
C14 C13 H13 120.0 . . ?
O3 C14 C13 114.6(5) . . ?
O3 C14 C15 125.2(6) . . ?
C15 C14 C13 120.2(5) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C0AA C17 P3 117.7(4) . . ?
C16 C17 P3 123.1(4) . . ?
C16 C17 C0AA 119.0(5) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O9 C31 H31A 109.9 . . ?
O9 C31 H31B 109.9 . . ?
O9 C31 C32 108.7(5) . . ?
H31A C31 H31B 108.3 . . ?
C32 C31 H31A 109.9 . . ?
C32 C31 H31B 109.9 . . ?
O8 C32 C31 112.6(5) . . ?
O8 C32 H32A 109.1 . . ?
O8 C32 H32B 109.1 . . ?
C31 C32 H32A 109.1 . . ?
C31 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
P5 S7 P4 105.63(8) . . ?
S3 P4 S7 105.72(9) . . ?
O12 P4 S3 117.52(18) . . ?
O12 P4 S7 106.36(17) . . ?
O12 P4 C20 102.4(2) . . ?
C20 P4 S3 116.6(2) . . ?
C20 P4 S7 107.58(17) . . ?
S6 P5 S7 106.69(9) . . ?
O11 P5 S6 117.17(17) . . ?
O11 P5 S7 106.20(17) . . ?
O11 P5 C11 98.8(2) . . ?
C11 P5 S6 117.87(19) . . ?
C11 P5 S7 109.4(2) . . ?
C23 O4 C19 118.3(5) . . ?
C8 O10 C33 117.7(5) . . ?
C28 O11 P5 124.4(3) . . ?
C27 O12 P4 122.1(4) . . ?
O10 C8 C9 114.2(5) . . ?
O10 C8 C29 125.7(5) . . ?
C29 C8 C9 120.1(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(5) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 P5 118.5(4) . . ?
C30 C11 P5 122.0(4) . . ?
C30 C11 C10 119.5(5) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 P4 122.2(4) . . ?
C21 C20 C25 118.6(5) . . ?
C25 C20 P4 118.9(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(6) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
O4 C23 C22 123.3(6) . . ?
O4 C23 C24 115.7(6) . . ?
C24 C23 C22 120.9(5) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(6) . . ?
C25 C24 H24 120.2 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.0(5) . . ?
C24 C25 H25 119.5 . . ?
O12 C27 H27A 109.8 . . ?
O12 C27 H27B 109.8 . . ?
O12 C27 C28 109.5(4) . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
O11 C28 C27 112.0(5) . . ?
O11 C28 H28A 109.2 . . ?
O11 C28 H28B 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C8 C29 H29 119.9 . . ?
C8 C29 C30 120.2(5) . . ?
C30 C29 H29 119.9 . . ?
C11 C30 H30 119.9 . . ?
C29 C30 C11 120.2(5) . . ?
C29 C30 H30 119.9 . . ?
O10 C33 H33A 109.5 . . ?
O10 C33 H33B 109.5 . . ?
O10 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 P2 O8 C32 61.8(5) . . . . ?
S1 P2 C1 C2 -27.4(5) . . . . ?
S1 P2 C1 C6 151.1(4) . . . . ?
S1 P3 O9 C31 -32.4(5) . . . . ?
S1 P3 C17 C0AA 79.9(5) . . . . ?
S1 P3 C17 C16 -95.5(5) . . . . ?
S4 P3 O9 C31 84.7(5) . . . . ?
S4 P3 C17 C0AA -38.5(5) . . . . ?
S4 P3 C17 C16 146.1(4) . . . . ?
S5 P2 O8 C32 -58.4(5) . . . . ?
S5 P2 C1 C2 94.8(5) . . . . ?
S5 P2 C1 C6 -86.7(5) . . . . ?
P2 O8 C32 C31 -74.1(6) . . . . ?
P2 C1 C2 C3 175.5(4) . . . . ?
P2 C1 C6 C5 -177.0(4) . . . . ?
P3 O9 C31 C32 102.2(5) . . . . ?
O1 C4 C5 C6 176.1(5) . . . . ?
O3 C14 C15 C16 -178.9(5) . . . . ?
O8 P2 C1 C2 -137.5(5) . . . . ?
O8 P2 C1 C6 41.0(5) . . . . ?
O9 P3 C17 C0AA -167.8(5) . . . . ?
O9 P3 C17 C16 16.8(5) . . . . ?
O9 C31 C32 O8 -33.3(7) . . . . ?
C1 P2 O8 C32 172.7(5) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C0AA C13 C14 O3 179.0(5) . . . . ?
C0AA C13 C14 C15 -0.9(9) . . . . ?
C2 C1 C6 C5 1.5(8) . . . . ?
C2 C3 C4 O1 -177.4(5) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C3 C4 C5 C6 -2.9(8) . . . . ?
C4 C5 C6 C1 1.4(9) . . . . ?
C6 C1 C2 C3 -3.0(9) . . . . ?
C7 O1 C4 C3 2.3(8) . . . . ?
C7 O1 C4 C5 -176.6(5) . . . . ?
C13 C0AA C17 P3 -176.1(5) . . . . ?
C13 C0AA C17 C16 -0.4(9) . . . . ?
C13 C14 C15 C16 1.0(9) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 P3 175.9(5) . . . . ?
C15 C16 C17 C0AA 0.5(9) . . . . ?
C17 P3 O9 C31 -146.8(4) . . . . ?
C17 C0AA C13 C14 0.6(9) . . . . ?
C18 O3 C14 C13 -179.0(6) . . . . ?
C18 O3 C14 C15 0.9(9) . . . . ?
S3 P4 O12 C27 84.1(4) . . . . ?
S3 P4 C20 C21 144.3(4) . . . . ?
S3 P4 C20 C25 -42.3(5) . . . . ?
S6 P5 O11 C28 -57.7(5) . . . . ?
S6 P5 C11 C10 -86.1(4) . . . . ?
S6 P5 C11 C30 94.2(5) . . . . ?
S7 P4 O12 C27 -34.0(5) . . . . ?
S7 P4 C20 C21 -97.2(4) . . . . ?
S7 P4 C20 C25 76.1(5) . . . . ?
S7 P5 O11 C28 61.3(4) . . . . ?
S7 P5 C11 C10 151.9(4) . . . . ?
S7 P5 C11 C30 -27.8(5) . . . . ?
P4 O12 C27 C28 101.8(5) . . . . ?
P4 C20 C21 C22 173.8(5) . . . . ?
P4 C20 C25 C24 -173.7(4) . . . . ?
P5 O11 C28 C27 -76.7(6) . . . . ?
P5 C11 C30 C29 178.7(4) . . . . ?
O4 C23 C24 C25 179.9(5) . . . . ?
O10 C8 C9 C10 177.8(5) . . . . ?
O10 C8 C29 C30 -177.6(5) . . . . ?
O11 P5 C11 C10 41.1(5) . . . . ?
O11 P5 C11 C30 -138.6(5) . . . . ?
O12 P4 C20 C21 14.6(5) . . . . ?
O12 P4 C20 C25 -172.0(4) . . . . ?
O12 C27 C28 O11 -30.1(6) . . . . ?
C8 C9 C10 C11 0.3(9) . . . . ?
C8 C29 C30 C11 -0.6(8) . . . . ?
C9 C8 C29 C30 2.0(9) . . . . ?
C9 C10 C11 P5 -178.6(4) . . . . ?
C9 C10 C11 C30 1.1(8) . . . . ?
C10 C11 C30 C29 -0.9(8) . . . . ?
C11 P5 O11 C28 174.6(5) . . . . ?
C19 O4 C23 C22 -1.5(9) . . . . ?
C19 O4 C23 C24 179.3(6) . . . . ?
C20 P4 O12 C27 -146.8(4) . . . . ?
C20 C21 C22 C23 -0.2(9) . . . . ?
C21 C20 C25 C24 -0.1(8) . . . . ?
C21 C22 C23 O4 -179.5(5) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C22 C23 C24 C25 0.6(9) . . . . ?
C23 C24 C25 C20 -0.4(9) . . . . ?
C25 C20 C21 C22 0.4(8) . . . . ?
C29 C8 C9 C10 -1.9(9) . . . . ?
C33 O10 C8 C9 -176.6(5) . . . . ?
C33 O10 C8 C29 3.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.80(11)
2 0.20(11)

